GB799778A - New n-alkyl-alkyl-piperidine-monocarboxylic acid amides and n-alkyl-alkyl-pyrrolidine-monocarboxylic acid amides - Google Patents
New n-alkyl-alkyl-piperidine-monocarboxylic acid amides and n-alkyl-alkyl-pyrrolidine-monocarboxylic acid amidesInfo
- Publication number
- GB799778A GB799778A GB4583/57A GB458357A GB799778A GB 799778 A GB799778 A GB 799778A GB 4583/57 A GB4583/57 A GB 4583/57A GB 458357 A GB458357 A GB 458357A GB 799778 A GB799778 A GB 799778A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- piperidine
- ethyl
- monocarboxylic acid
- pyrrolidine
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 abstract 2
- AXAOTHQUPORHQV-UHFFFAOYSA-N 1,5-diethylpiperidine-2-carboxylic acid Chemical compound C(C)N1C(CCC(C1)CC)C(=O)O AXAOTHQUPORHQV-UHFFFAOYSA-N 0.000 abstract 1
- CCXSOWFCDHIWRN-UHFFFAOYSA-N 1-ethyl-5-methylpiperidine-2-carboxylic acid Chemical compound C(C)N1C(CCC(C1)C)C(=O)O CCXSOWFCDHIWRN-UHFFFAOYSA-N 0.000 abstract 1
- VNSFRNQGPLODIO-UHFFFAOYSA-N 1-ethyl-5-methylpyrrolidine-2-carboxylic acid Chemical compound CCN1C(C)CCC1C(O)=O VNSFRNQGPLODIO-UHFFFAOYSA-N 0.000 abstract 1
- NEVOZQVGAWLVNT-UHFFFAOYSA-N 1-ethyl-6-methylpiperidine-3-carboxylic acid Chemical compound C(C)N1CC(CCC1C)C(=O)O NEVOZQVGAWLVNT-UHFFFAOYSA-N 0.000 abstract 1
- LBUPWCHXRSTTNO-UHFFFAOYSA-N 2,2-dimethylpiperidine Chemical compound CC1(C)CCCCN1 LBUPWCHXRSTTNO-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 150000001448 anilines Chemical class 0.000 abstract 1
- 150000001555 benzenes Chemical group 0.000 abstract 1
- -1 chloro-substituted benzene ring Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises (1) N-alkyl-alkyl-piperidine-monocarboxylic acid amides in which the acid amide group is in the 3- or 4-position and N-alkyl-alkyl-pyrrolidine-b -monocarboxylic acid amides of the formul\mg <FORM:0799778/IV (b)/1> respectively, wherein R1 is an alkyl group, R2 and R3 are each an alkyl group or one is alkyl and the other is hydrogen, and Ar is an unsubstituted benzene ring or an alkyl, alkoxy, hydroxy and/or chloro-substituted benzene ring, and acid addition salts thereof; and (2) the preparation of N-alkyl-alkyl-piperidine-monocarboxylic acid amides in which the acid amide group is in the 2-, 3- or 4-position and N-alkyl-alkyl-pyrrolidine-monocarboxylic acid amides of the formul\mg <FORM:0799778/IV (b)/2> respectively, by reacting an appropriate alkyl-piperidine-monocarboxylic acid or alkyl-pyrrolidine-monocarboxylic acid, which may or may not be N-alkylated, or the anhydride, ester, or halide of such an acid, preferably in the form of the hydrochloride, with aniline or an appropriately substituted aniline or with phenyl isocyanate or an appropriately substituted phenyl isocyanate and, when necessary, alkylating the nuclear nitrogen atom. Preferred compounds are those in which Ar is substituted with an alkyl group or chlorine in the 2-position, with or without a hydroxy, alkyl or alkoxy group in the 4-position and with or without chlorine or an alkyl or alkoxy group in the 6-position. The examples describe the preparation of N-ethyl-5-ethyl - piperidine - 2 - carboxylic acid - 2 : 6 - xylidide, N - ethyl - 6 - methyl - piperidine - 3 - carboxylic acid - 2 : 6 - xylidide, N - methyl-2 : 6 - dimethyl - piperidine - 4 - carboxylic acid-2 - ethyl - anilide, N - ethyl - 5 - methyl - pyrrolidine - 2 - carboxylic acid - 2 : 6 - xylidide, N-n-propyl - 5 - ethyl - pyrollidine - 2 - carboxylic acid - 2 - ethoxy - anilide and N - ethyl - 5 - methyl - piperidine - 2 - carboxylic acid - 2 : 6-xylidide. Specification 799,780 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE170156 | 1956-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB799778A true GB799778A (en) | 1958-08-13 |
Family
ID=38526955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4583/57A Expired GB799778A (en) | 1956-02-22 | 1957-02-11 | New n-alkyl-alkyl-piperidine-monocarboxylic acid amides and n-alkyl-alkyl-pyrrolidine-monocarboxylic acid amides |
Country Status (7)
| Country | Link |
|---|---|
| BE (2) | BE554777A (en) |
| DE (2) | DE1228613B (en) |
| DK (3) | DK87391C (en) |
| ES (1) | ES234060A1 (en) |
| FR (1) | FR1225621A (en) |
| GB (1) | GB799778A (en) |
| NL (1) | NL98233C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3138614A (en) * | 1961-12-18 | 1964-06-23 | Lilly Co Eli | Salts of 1, 1-dimethyl-3-pyrrolidyl phenyl-2-thienylglycolate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT180259B (en) * | 1952-02-25 | 1954-11-25 | Cilag Ag | Process for the preparation of new basic substituted fatty acid-2-halogen-6-methylanilides and their salts |
-
1957
- 1957-02-06 BE BE554777A patent/BE554777A/en unknown
- 1957-02-08 BE BE554837A patent/BE554837A/en unknown
- 1957-02-11 GB GB4583/57A patent/GB799778A/en not_active Expired
- 1957-02-14 DE DEA26583A patent/DE1228613B/en active Pending
- 1957-02-14 DE DEA26584A patent/DE1229091B/en active Pending
- 1957-02-18 FR FR732024A patent/FR1225621A/en not_active Expired
- 1957-02-21 DK DK65057AA patent/DK87391C/en active
- 1957-02-21 DK DK65257AA patent/DK86988C/en active
- 1957-02-21 DK DK65157AA patent/DK88970C/en active
- 1957-02-21 NL NL214800A patent/NL98233C/en active
- 1957-02-22 ES ES0234060A patent/ES234060A1/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3138614A (en) * | 1961-12-18 | 1964-06-23 | Lilly Co Eli | Salts of 1, 1-dimethyl-3-pyrrolidyl phenyl-2-thienylglycolate |
Also Published As
| Publication number | Publication date |
|---|---|
| NL98233C (en) | 1961-06-15 |
| ES234060A1 (en) | 1957-11-01 |
| DK88970C (en) | 1960-05-16 |
| FR1225621A (en) | 1960-07-01 |
| DE1228613B (en) | 1966-11-17 |
| BE554837A (en) | 1960-02-12 |
| DK86988C (en) | 1959-03-09 |
| DE1229091B (en) | 1966-11-24 |
| DK87391C (en) | 1959-06-08 |
| BE554777A (en) | 1960-01-29 |
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