GB765849A - Improvements in or relating to new aminoalkyl phenyl ethers - Google Patents
Improvements in or relating to new aminoalkyl phenyl ethersInfo
- Publication number
- GB765849A GB765849A GB26040/53A GB2604053A GB765849A GB 765849 A GB765849 A GB 765849A GB 26040/53 A GB26040/53 A GB 26040/53A GB 2604053 A GB2604053 A GB 2604053A GB 765849 A GB765849 A GB 765849A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- reacting
- reaction
- compounds
- lower alkyl
- 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 aminoalkyl phenyl ethers Chemical class 0.000 title abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 7
- 238000006243 chemical reaction Methods 0.000 abstract 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- JEFSTMHERNSDBC-UHFFFAOYSA-N 1,2-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC=CCC1(C)O JEFSTMHERNSDBC-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- JRPNCILONFCLQX-UHFFFAOYSA-N 1,2-dichloro-n,n-dimethylethanamine Chemical compound CN(C)C(Cl)CCl JRPNCILONFCLQX-UHFFFAOYSA-N 0.000 abstract 2
- SCWBSTVOWDDYHH-UHFFFAOYSA-N 4-amino-2,6-dichlorophenol;4-aminophenol Chemical compound NC1=CC=C(O)C=C1.NC1=CC(Cl)=C(O)C(Cl)=C1 SCWBSTVOWDDYHH-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 238000001640 fractional crystallisation Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 abstract 1
- BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 abstract 1
- WNKXRJOYUCAQLE-UHFFFAOYSA-N 2-chloro-n,n-diethylpropan-1-amine;hydrochloride Chemical compound Cl.CCN(CC)CC(C)Cl WNKXRJOYUCAQLE-UHFFFAOYSA-N 0.000 abstract 1
- GYXWNSDLDXGMGU-UHFFFAOYSA-N 2-chloro-n,n-dimethylpropan-1-amine Chemical compound CC(Cl)CN(C)C GYXWNSDLDXGMGU-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
- VTKPSXWRUGCOAC-GUBZILKMSA-N Met-Ala-Met Chemical compound CSCC[C@H](N)C(=O)N[C@@H](C)C(=O)N[C@H](C(O)=O)CCSC VTKPSXWRUGCOAC-GUBZILKMSA-N 0.000 abstract 1
- 101100109871 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-8 gene Proteins 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000003708 ampul Substances 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 239000012043 crude product Substances 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 150000003385 sodium Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the formula: <FORM:0765849/IV(b)/1> in which R1 and R2 are the same or different and are lower alkyl groups or chlorine atoms and R3 is a hydrogen atom or, where one or both of R1 and R3 are lower alkyl groups, a lower alkyl group, A represents a divalent group selected from -CH2-CH2-, <FORM:0765849/IV(b)/2> and R4 and R5 each represent a lower alkyl group (i.e. having up to 6 carbon atoms). Such compounds are obtainable by reacting a compound of the formula: <FORM:0765849/IV(b)/3> with a compound of the formula Y-Z where X, Y and Z represent atoms or groups such that X will react with Y-Z to form the group: <FORM:0765849/IV(b)/4> or a group readily convertible into such grouping, and in the latter case effecting such a conversion. "Convertible" groupings include -A-NH2, A.NHR4, -A-Halogen and A1CO. NR4R5 where A1 represents a group differing from A by a CH2 group. In the preferred process a phenol: <FORM:0765849/IV(b)/5> is reacted with a dialkylaminoalkyl halide of the formula Hal.A.NR3R4. Alternative methods are (a) reaction of the appropriate ester with an amine HNR4R5, (b) reduction of the corresponding amide, (c) alkylation of the corresponding primary or secondary amine. Where A is a branched chain, isomerization may occur during the reaction, the two isomers formed being separable by fractional crystalllization of their hydrochlorides. The starting materials can be prepared by reaction of the appropriate phenol ArOH with the appropriate basic ester to give Ar-O-A-NHR4 or Ar-O-A-NR4R5. Compounds of the type Ar-O-A-M (where M represents an ester group) are obtained by reacting the phenol with a diester M-A-M. Compounds of the type Ar-O-A1-CONR4R5 are obtained by reacting the appropriate phenol with an amide ester of the type M-A1-CONR4R5. In examples: (1) 2 - (b - dimethylaminoethoxy) - 1 : 3 - dichlorobenzene hydrochloride is prepared by the reaction of 2 : 6-dichlorophenol in aqueous sodium hydroxide solution with b -dimethylaminoethyl chloride hydrochloride; (2) the same product is obtained by reacting the sodium derivative of 2 : 6-dichlorophenol in acetone solution with an ethereal solution of b -dimethylaminoethyl chloride. Similarly obtained are (3) 2-(21-dimethylamino - 11 - methylethoxy) - 1 : 3 - dimethyl benzene hydrochloride (by fractional crystallization from the crude product from 2 : 6-xylenol and 3 - dimethylamino - 2 - chloropropane; (4) a mixture of 2 - (21 - diethylamino - 21-methylethoxy) - 1 : 3 - dimethylbenzene and 2-(21 - diethylamino - 11 - methylethoxy) - 1 : 3-dimethylbenzene (which is separated into its components by fractional crystallization) from 2 : 6-xylenol and 3-diethylamino-2-chloropropane hydrochloride; (5) b - (2 : 6 - xylyloxy)-ethyldimethylamine and b - (2 : 6 - xylyloxy) ethyldiethylamine, which are converted to hydrobromides. The two latter compounds can also be prepared by reacting the corresponding aryloxyethyl bromide with excess ethereal dimethylamine or diethylamine in a sealed ampoule at room temperature. The Provisional Specification also describes the reaction of 2 : 6-xylenol and 2 : 4 : 6-mesitol with 1 : 2-dibromoethane to give b -(2 : 6-xylyloxy)-ethyl bromide and b -(2 : 4 : 6-mesityloxy)-ethyl bromide respectively. Specification 687,189 is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB26040/53A GB765849A (en) | 1953-09-21 | 1953-09-21 | Improvements in or relating to new aminoalkyl phenyl ethers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB26040/53A GB765849A (en) | 1953-09-21 | 1953-09-21 | Improvements in or relating to new aminoalkyl phenyl ethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB765849A true GB765849A (en) | 1957-01-16 |
Family
ID=10237415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26040/53A Expired GB765849A (en) | 1953-09-21 | 1953-09-21 | Improvements in or relating to new aminoalkyl phenyl ethers |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB765849A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1185196B (en) * | 1959-05-29 | 1965-01-14 | Sterling Drug Inc | Process for the preparation of new aminoalkoxyaniline derivatives |
| US3205136A (en) * | 1962-12-24 | 1965-09-07 | Smith Kline French Lab | Antidepressant phenyloxyalkylamines |
| US6887871B2 (en) | 2000-02-23 | 2005-05-03 | Astrazeneca Ab | Use of phenylheteroakylamine derivatives |
| US6900243B2 (en) | 2000-02-23 | 2005-05-31 | Astrazeneca Ab | Phenylheteroalkylamine derivatives |
| US6953797B2 (en) | 2000-02-23 | 2005-10-11 | Astrazeneca Ab | Use of phenylheteroalkylamine derivatives |
| US7223794B2 (en) | 2001-07-31 | 2007-05-29 | Astrazeneca Ab | Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase |
-
1953
- 1953-09-21 GB GB26040/53A patent/GB765849A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1185196B (en) * | 1959-05-29 | 1965-01-14 | Sterling Drug Inc | Process for the preparation of new aminoalkoxyaniline derivatives |
| US3205136A (en) * | 1962-12-24 | 1965-09-07 | Smith Kline French Lab | Antidepressant phenyloxyalkylamines |
| US6887871B2 (en) | 2000-02-23 | 2005-05-03 | Astrazeneca Ab | Use of phenylheteroakylamine derivatives |
| US6900243B2 (en) | 2000-02-23 | 2005-05-31 | Astrazeneca Ab | Phenylheteroalkylamine derivatives |
| US6953797B2 (en) | 2000-02-23 | 2005-10-11 | Astrazeneca Ab | Use of phenylheteroalkylamine derivatives |
| US7223794B2 (en) | 2001-07-31 | 2007-05-29 | Astrazeneca Ab | Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase |
| WO2003011210A3 (en) * | 2001-07-31 | 2007-10-25 | Astrazeneca Ab | Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase |
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