GB705652A - Manufacture of 3-aminopropane compounds - Google Patents

Manufacture of 3-aminopropane compounds

Info

Publication number
GB705652A
GB705652A GB24281/49A GB2428149A GB705652A GB 705652 A GB705652 A GB 705652A GB 24281/49 A GB24281/49 A GB 24281/49A GB 2428149 A GB2428149 A GB 2428149A GB 705652 A GB705652 A GB 705652A
Authority
GB
United Kingdom
Prior art keywords
indolyl
methyl
cyano
radical
methylindolyl
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
Application number
GB24281/49A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Farbwerke Hoechst AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Farbwerke Hoechst AG filed Critical Farbwerke Hoechst AG
Publication of GB705652A publication Critical patent/GB705652A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical

Abstract

The invention comprises compounds of the general formula R1 R2 CH-CH2-CH2 -N(R3)2 in which R1 and R2 represent a substituted or unsubstituted aromatic or heterocyclic radical and at least one of R1 and R2 represents an indolyl radical and R3 represents hydrogen or a methyl group, and salts of such compounds. They are obtained by reacting an organo-magnesium halide of the formula R1-Mg-halogen with an a -cyano-acrylic acid alkyl ester of the formula R2-CH=C (CN)-COO alkyl to form a b :b -disubstituted a -cyano-propionic acid ester containing an indolyl radical as at least one of the b -substituents, converting the ester by hydrolysis and decarboxylation into the corresponding nitrile, hydrogenating the nitrile to the amine, and if desired, methylating the amine. As starting materials are mentioned a -cyano-acrylic acid ethyl esters containing in the b -position a thienyl-(2)-, furyl-(2)-, pyridyl-(2)- or (3)-, quinolyl-(2) or (4)-, quinoxalyl -(2)-, indolyl -(3)-, 2-methylindolyl-(3)-, N-methyl-triazolyl-(2)-, p N-methylpyrrole-(2)-, phenyl-, fluorophenyl-, chlorophenyl-, iodophenyl-, p-anisyl-, or a naphthyl -(1) or (2)-radical. Organo-magnesium halides are mentioned in which the organic radical is a phenyl, b -indolyl-, p-chlorophenyl-, p-fluorophenyl-, p-anisyl-, naphthyl -(1) or (2)-, 4-fluoronaphthyl -(1)-, 4-methoxy-naphthyl -(1)-, 2-methyl -b - indolyl or an a - thienyl radical. Methylation may be effected by reaction with formaldehyde and formic acid or by concurrent catalytic hydrogenation and reaction with formaldehyde. In examples (1) a -cyano-cinnamic acid methyl ester is reacted with b -indolyl magnesium bromide to give a -cyano-b -phenyl-b - [indolyl- (3)] -propio-nitrile and the latter is hydrogenated to 1-phenyl- 1- indolyl -b - propylamine -(3); a similar process to (1), using b -2-methyl -indolyl magnesium bromide yields 1-phenyl -1- [(21)-methyl-indolyl -(31)] -3- aminopropane hydrochloride; (3) a - cyanom-methoxycinnamic acid methyl ester and b - 2- methyl-indolyl magnesium bromide are reacted and worked up as in (1) to give b -2- methyl -indolyl -b -m-methoxyphenylpropionitrile, which is reduced to 1- (m-methoxyphenyl) -1- (21-methylindolyl)-3-aminopropane hydrochloride; (4) a - cyano -b - thienylacrylic acid methyl ester and b - 2- methylindolyl magnesium bromide are reacted to give a - cyano -b -thienyl -b - 2-methylindolyl propionic acid methyl ester which is hydrolysed with sodium hydroxide and the product decarboxylated by heating in quinoline to give b - 2-methylindolyl -b - thienyl propionitrile, which on reduction gives 1- thienyl- 1- (21- methyl) -indolyl -3-aminopropane hydrochloride. Specification 646,198 (as open to public inspection under Sect. 91) is referred to.
GB24281/49A 1948-10-01 1950-09-19 Manufacture of 3-aminopropane compounds Expired GB705652A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE705652X 1948-10-01

Publications (1)

Publication Number Publication Date
GB705652A true GB705652A (en) 1954-03-17

Family

ID=6616965

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24281/49A Expired GB705652A (en) 1948-10-01 1950-09-19 Manufacture of 3-aminopropane compounds

Country Status (1)

Country Link
GB (1) GB705652A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005118539A1 (en) * 2004-06-01 2005-12-15 F.Hoffmann-La Roche Ag 3-amino-1-arylpropyl indoles as monoamine reuptake inhibitor
US7446118B2 (en) 2005-11-30 2008-11-04 Roche Palo Alto Llc 3-amino-1-arylpropyl indoles and aza-substituted indoles and uses thereof
US7598399B2 (en) 2005-11-30 2009-10-06 Roche Palo Alto Llc Methods for synthesis of 3-amino-1-arylpropyl indoles
US7638517B2 (en) 2005-11-30 2009-12-29 Roche Palo Alto Llc 3-Amino-1-arylpropyl azaindoles and uses thereof
WO2012097744A1 (en) * 2011-01-20 2012-07-26 Merck Sharp & Dohme Corp. Mineralocorticoid receptor antagonists

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7863305B2 (en) 2004-06-01 2011-01-04 Roche Palo Alto Llc 3-amino-1-arylpropyl indoles as monoamine reuptake inhibitors
JP2008500983A (en) * 2004-06-01 2008-01-17 エフ．ホフマン−ラ　ロシュ　アーゲー 3-Amino-1-arylpropylindoles as monoamine reuptake inhibitors
JP4698671B2 (en) * 2004-06-01 2011-06-08 エフ．ホフマン−ラ ロシュ アーゲー 3-Amino-1-arylpropylindoles as monoamine reuptake inhibitors
WO2005118539A1 (en) * 2004-06-01 2005-12-15 F.Hoffmann-La Roche Ag 3-amino-1-arylpropyl indoles as monoamine reuptake inhibitor
AU2005250116B2 (en) * 2004-06-01 2011-01-20 F. Hoffmann-La Roche Ag 3-amino-1-arylpropyl indoles as monoamine reuptake inhibitor
US7598399B2 (en) 2005-11-30 2009-10-06 Roche Palo Alto Llc Methods for synthesis of 3-amino-1-arylpropyl indoles
US7803830B2 (en) 2005-11-30 2010-09-28 Roche Palo Alto Llc 3-amino-1-arylpropyl indoles and AZA-substituted indoles and uses thereof
US7638517B2 (en) 2005-11-30 2009-12-29 Roche Palo Alto Llc 3-Amino-1-arylpropyl azaindoles and uses thereof
US7446118B2 (en) 2005-11-30 2008-11-04 Roche Palo Alto Llc 3-amino-1-arylpropyl indoles and aza-substituted indoles and uses thereof
WO2012097744A1 (en) * 2011-01-20 2012-07-26 Merck Sharp & Dohme Corp. Mineralocorticoid receptor antagonists
CN103384661A (en) * 2011-01-20 2013-11-06 默沙东公司 Mineralocorticoid receptor antagonists
JP2014502979A (en) * 2011-01-20 2014-02-06 メルク・シャープ・アンド・ドーム・コーポレーション Mineralocorticoid receptor antagonist
US8933113B2 (en) 2011-01-20 2015-01-13 Merck Sharp & Dohme Corp. Mineralocorticoid receptor antagonists
US9403807B2 (en) 2011-01-20 2016-08-02 Merck Sharp & Dohme Corp. Mineralocorticoid receptor antagonists
RU2598842C2 (en) * 2011-01-20 2016-09-27 Мерк Шарп Энд Домэ Корп. Mineralocorticoid receptor antagonists

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