GB586135A - Manufacture of acylated aliphatic amino carboxylic acid amides - Google Patents
Manufacture of acylated aliphatic amino carboxylic acid amidesInfo
- Publication number
- GB586135A GB586135A GB21216/43A GB2121643A GB586135A GB 586135 A GB586135 A GB 586135A GB 21216/43 A GB21216/43 A GB 21216/43A GB 2121643 A GB2121643 A GB 2121643A GB 586135 A GB586135 A GB 586135A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- acylated
- chloride
- ethylamino
- amide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 acylated aliphatic amino carboxylic acid amides Chemical class 0.000 title abstract 16
- 238000004519 manufacturing process Methods 0.000 title 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 15
- 150000001875 compounds Chemical class 0.000 abstract 9
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 8
- 229940095574 propionic acid Drugs 0.000 abstract 8
- 125000001931 aliphatic group Chemical group 0.000 abstract 7
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 abstract 7
- 235000019260 propionic acid Nutrition 0.000 abstract 7
- ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 6
- 150000001408 amides Chemical class 0.000 abstract 5
- YKOQQFDCCBKROY-UHFFFAOYSA-N n,n-diethylpropanamide Chemical compound CCN(CC)C(=O)CC YKOQQFDCCBKROY-UHFFFAOYSA-N 0.000 abstract 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- 150000001735 carboxylic acids Chemical class 0.000 abstract 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 abstract 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 abstract 2
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 125000003368 amide group Chemical group 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 229940124277 aminobutyric acid Drugs 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 2
- 229960002449 glycine Drugs 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- CDQSTBHGKNNPSY-UHFFFAOYSA-N n,n-diethylbutanamide Chemical compound CCCC(=O)N(CC)CC CDQSTBHGKNNPSY-UHFFFAOYSA-N 0.000 abstract 2
- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical group CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 abstract 2
- 229960003512 nicotinic acid Drugs 0.000 abstract 2
- 235000001968 nicotinic acid Nutrition 0.000 abstract 2
- 239000011664 nicotinic acid Substances 0.000 abstract 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 2
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 abstract 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- GOHANHUTUQJHKC-UHFFFAOYSA-N 2-amino-n,n-diethyl-4-methylpentanamide Chemical compound CCN(CC)C(=O)C(N)CC(C)C GOHANHUTUQJHKC-UHFFFAOYSA-N 0.000 abstract 1
- WXYGMIMPKDAELC-UHFFFAOYSA-N 2-amino-n,n-diethylbutanamide Chemical compound CCC(N)C(=O)N(CC)CC WXYGMIMPKDAELC-UHFFFAOYSA-N 0.000 abstract 1
- CQQUWTMMFMJEFE-UHFFFAOYSA-N 2-chloro-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CCl CQQUWTMMFMJEFE-UHFFFAOYSA-N 0.000 abstract 1
- SMUKODJVMQOSAB-UHFFFAOYSA-N 2-ethylbutanoyl chloride Chemical compound CCC(CC)C(Cl)=O SMUKODJVMQOSAB-UHFFFAOYSA-N 0.000 abstract 1
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 abstract 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 abstract 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 abstract 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical group CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 229960001138 acetylsalicylic acid Drugs 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical group 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 239000002269 analeptic agent Substances 0.000 abstract 1
- 230000003555 analeptic effect Effects 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 abstract 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 abstract 1
- 150000001714 carbamic acid halides Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 abstract 1
- HBJKJBHQKGRVHW-UHFFFAOYSA-N ethanamine;propan-1-amine Chemical compound CCN.CCCN HBJKJBHQKGRVHW-UHFFFAOYSA-N 0.000 abstract 1
- HFEJENNUKAUMMS-UHFFFAOYSA-N ethyl 2-(ethylamino)butanoate Chemical compound CCNC(CC)C(=O)OCC HFEJENNUKAUMMS-UHFFFAOYSA-N 0.000 abstract 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 1
- 229940093858 ethyl acetoacetate Drugs 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 abstract 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- SYQIOQBWHUGNLQ-UHFFFAOYSA-N n,n-diethyl-2-(ethylamino)-2-methylpropanamide Chemical compound CCNC(C)(C)C(=O)N(CC)CC SYQIOQBWHUGNLQ-UHFFFAOYSA-N 0.000 abstract 1
- NVSDUTPNZRIEMZ-UHFFFAOYSA-N n,n-diethyl-2-(ethylamino)acetamide Chemical compound CCNCC(=O)N(CC)CC NVSDUTPNZRIEMZ-UHFFFAOYSA-N 0.000 abstract 1
- CLJWSVLSCYWCMP-UHFFFAOYSA-N n,n-diethyl-2-methylpropanamide Chemical compound CCN(CC)C(=O)C(C)C CLJWSVLSCYWCMP-UHFFFAOYSA-N 0.000 abstract 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 abstract 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical group C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 229940081066 picolinic acid Drugs 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 abstract 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 abstract 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 1
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Acylated aliphatic aminocarboxylic acid amides of the general formula <FORM:0586135/IV/1> wherein R is an alkyl or cycloalkyl group, Ro is an alkyl group which may be linked to R by a carbon or hetero atom, A is an alkylene group, R1 is an acyl radical of a carboxylic acid and R11 is an alkyl or cycloalkyl group, are prepared by acylating aliphatic N-monoalkyl- or N-cycloalkyl-amino carboxylic acid amides of the formula <FORM:0586135/IV/2> with carboxylic acids or their functional derivatives. In modifications, the compounds may also be prepared by reacting aliphatic N-alkyl- or N-cycloalkyl amino carboxylic acids or their functional derivatives, acylated by carboxylic acids, with secondary aliphatic or cycloaliphatic or heterocylcic amines with endocyclic amino groups; by reacting salts of the acylated aliphatic amino carboxylic acids with carbamic acid halides derived from the above mentioned secondary amines; by reacting monoalkyl or monocycloalkyl amides of carboxylic acids with aliphatic a - or b -halogen carboxylic acid amides of which the amide groups are twice substituted by the groups R and Ro defined above; and by reacting acylated aliphatic amino carboxylic acid amides, which in the amino and/or the amide group still contain replaceable hydrogen atoms, by replacing said hydrogen atoms by an alkali metal atom, for example, by means of sodium metal or sodamide and then reacting with alkylating or cycloalkylating agents. The compounds are stated to be novel and are suitable for therapeutic use, especially as analeptics, and some may be used as solvent promoters. In examples: (1) ethylamino acetic acid diethyl amide, prepared by reacting chloracetic acid diethyl amide with ethyl amine, is acylated with diethyl acetic acid chloride yielding the ethyl amino acetic acid diethyl amide as its hydrochloride, the base being liberated on treatment with alkali; (2) isobutyl amino acetic acid diethyl amide is acylated with diethyl oxamic acid chloride yielding N-diethyl oxaminoyl-isobutyl amino acetic acid diethyl amide (hydrochloride); (3) cyclohexyl amin acetic acid diethyl amide is acylated with diethyl oxamic acid chloride yielding N-diethyloxaminoyl - cyclohexyl - amino - acetic acid diethyl amide (hydroxhloride), and analogous cyclopentyl compounds such as N-dimethyloxaminoyl-cyclopentyl-amino-acetic acid diethyl amide may be prepared likewise. Table I gives further examples of compounds of the type <FORM:0586135/IV/3> (4) a -methyl amino propionic acid diethylamide is acylated with dimethyl carbamic acid chloride yielding an acylated amide of the type <FORM:0586135/IV/4> further examples being given in Table 2; (5) a -ethyl amino propionic acid diethyl amide is acylated with isovaleric acid chloride, the product being of the type <FORM:0586135/IV/5> of which further examples appear in Table 3; (6) a -allyl amino propionic acid diethyl amide is acylated with isovaleric acid chloride, analogous products being obtained using b : b -dimethyl acrylic acid chloride and diethyl oxamic acid chloride; (7) a -n-butyl amino propionic acid diethyl amide is acylated with dimethyl acroyl chloride; similar products of the type <FORM:0586135/IV/6> are given in Table 4; (8)a -sec.-butyl amino propionic acid diethyl amide is acylated with dimethyl acroyl chloride and an analogous compound is obtained using diethyl oxamic acid chloride; (9) b -ethyl amino propionic acid diethylamide is acylated with trimethylacetic acid chloride and further compounds of this type <FORM:0586135/IV/7> are described in Table 5; (10) b -allyl amino propionic acid diethyl amide is acylated with dimethyl acroyl chloride or alternatively with N-diethyl oxamic acid chloride; b -allyl amino propionic acid dimethyl amide is similarly acylated with isovaleric acid; (11)-(16) a -methylamino-, a -ethylamino-, a -allylamino-, a -isopropylamino-, and n-butylaminon-butyric acid diethyl (or dimethyl) amides are acylated with dimethyl acroyl chloride, isovaleric acid chloride or diethyl oxamic acid chloride and analogous compounds are described in Tables 6-9, of the types <FORM:0586135/IV/8> and <FORM:0586135/IV/9> ; (17) ethylamino isobutyric acid diethyl amide, from ethyl amine and a -bromisobutyric acid diethylamide, is acylated with isobutyric acid chloride, other examples of products of the type <FORM:0586135/IV/100> being given in Table 10; (18) a -ethylamino- or a -methylamino-isovaleric acid diethyl amide is acylated with diethyl oxamic acid chloride; (19) a -ethylamino-n-valeric acid diethyl amide is acylated with acetyl chloride; similar compounds of the type <FORM:0586135/IV/111> are described in Table 11; (20) a -ethylamino-n-caproic acid dimethyl amide is acylated with isovaleric acid chloride; (Table 12 describes similar compounds of the type <FORM:0586135/IV/122> (21) ethylamino-n-butyric acid ethyl ester, from ethyl amine and a -bromo-n-butyric ethyl ester, is reacted with isovaleric acid chloride, and the resulting N-isovaleroyl-a -ethylamino-n-butyric acid ester hydrolysed, converted into the acid chloride by means of phosphorus pentachloride and then treated with diethylamine; the same acylated disubstituted amide may also be formed from a -ethylamino butyric acid diethyl amide and isovaleric acid chloride; (22) N-n-butyroyl-a -aminobutyric acid diethylamide, from a -aminobutyric acid diethyl amide and n-butyryl chloride, is heated with sodamide and then alkylated by means of ethyl iodide; the same product may be obtained by triethylating n - butyroyl - a - aminobutyric acid amide or by the method of (1) above. In addition to the already mentioned staring materials, there are specified for the acylation, inter alia, crotonic acid, sorbinic acid, phenyl acetic acid, 3 : 4-dimethoxy-benzoic acid, picolinic acid, nicotinic acid, 3 : 5-dimethyl-isoxazol-4-carboxylic acid, furan carboxylic acid, pyrazine carboxylic acid, acetyl salicylic acid and 4 : 6-dimethyl cumalinic acid (prepared from ethyl aceto-acetate by means of sulphuric acid). The N-alkyl or N-cycloalkylated aliphatic amino carboxy amides may be prepared by reaction of aliphatic a - or b -halogen carboxyamides with primary aliphatic or cycloaliphatic amines such as methylamine, ethylamine propyl amine, isopropyl amine, allyl amine and cyclohexylamine; the halogen carboxy amides themselves may be prepared by reacting the corresponding acids or their functional derivatives with secondary aliphatic, cycloaliphatic or heterocylic amines with endocyclic amino groups such as dimethylamine, diethylamine, diallyl amine, methyl-propyl amine, methylcyclohexyl amine, piperidine and morpholine. Samples have been furnished under Sect. 2 (5) of the following compounds: (1) N-(3 : 4-dimethoxybenzoyl) - ethylamino acetic acid-diethyl amide; (2) b -[N-(o-acetoxybenzoyl)-ethylamino] propionic acid diethylamide; (3) b - [N - (3 : 4 - dimethoxy - benzoyl) ethylamino] propionic acid diethylamide; (4) a -[N-(3 : 5-dimethyl-isoxazol-carboxylic acid) ethylamino]-butyric acid diethylamide; (5) a -[N-(2 : 4-dimethyl-coumalinic acid) diethylamino] isobutyric acid diethylamide; (6) a -[N-(nicotinic acid)-isopropylamino] butyric acid diethylamide; (7) a -[N-(2-furan-carboxylic acid)-ethylamino] propionic acid diethylamide; (8) a -[N-(b 1-chloro-b 1-methyl-acroyl) -ethylamino]-propionic acid diethylamide; (9) a - [N - (b - chloro - b - methyl - acroyl) - propylamino] - pro - pionic acid dimethylamide; (10) a -[N-(b -chloro-b - methyl - acroyl) - methylamino] butyric acid diethylamide; all these products were prepared according to example (1) above; (11) a -[N-(b -chloro-b -methyl-acroyl) ethylamino] - propionic acid dimethylamide, prepared by acylating a -ethylamino propionic acid ethyl ester with b -chloro-b -methyl acroyl chloride, saponifying with caustic soda and reacting the resulting salt with dimethyl carbamic acid chloride; (12) a - [N - (b : b - dimethyl - acroyl) - ethylamino] - butyric acid morpholide, from a -ethylamino butyric acid morpholide (obtained by reacting a -bromo-butyric acid morpholide with ethylamine) and b : b -dimethyl-acroyl chloride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH586135X | 1942-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB586135A true GB586135A (en) | 1947-03-07 |
Family
ID=4521815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21216/43A Expired GB586135A (en) | 1942-12-18 | 1943-12-17 | Manufacture of acylated aliphatic amino carboxylic acid amides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB586135A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116462602A (en) * | 2023-04-28 | 2023-07-21 | 盐城工学院 | Amino acid surfactant and preparation method thereof |
-
1943
- 1943-12-17 GB GB21216/43A patent/GB586135A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116462602A (en) * | 2023-04-28 | 2023-07-21 | 盐城工学院 | Amino acid surfactant and preparation method thereof |
| CN116462602B (en) * | 2023-04-28 | 2024-06-14 | 盐城工学院 | Amino acid surfactant and preparation method thereof |
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