GB760023A - Process for the production of anilides of ªÏ-dialkylaminoalkyl carboxylic acids - Google Patents

Abstract

Compounds of the general formula <FORM:0760023/IV(b)/1> wherein R1-R5 may be hydrogen or alkyl, aryl or alkoxy groups, at least R1 or R5 being one of such groups, R6 is an alkylene group and R7 and R8 are alkyl groups or jointly denote a hydrocarbon group, the carbon atoms of which together with the nitrogen atom form a ring, are made by reacting aniline, substituted as above in at least one of the ortho positions, with a mixed anhydride of the corresponding dialkylaminocarboxylic acid and benzoic or benzene sulphonic acid. The mixed anhydride may be prepared by reacting a salt of dialkylaminocarboxylic acid with a halide (e.g. the chloride) of benzoic or benzenesulphonic acid in an anhydrous organic solvent and suitably the substituted aniline is added directly to the resulting reaction mixture. In examples: (1) sodium diethylaminoacetate is treated with benzoyl chloride in trichloroethylene and 2 : 6-dimethylaniline is added to the reaction product to give o - diethylamino - 2 : 6 - dimethylacetanilide; (2) the mixed anhydride of diethylaminoacetic acid and benzoic acid is reacted with 2 : 4 : 6 - trimethylaniline to give o - diethylamino - 2 : 4 : 6 - trimethylacetanilide; (3) the mixed anhydride of diethylaminoacetic acid and benzoic acid is reacted with 2-amino-diphenyl to give o -diethylamino-2 -phenylacetanilide; (4) sodium diethylaminoacetate is reacted with benzenesulphonyl chloride in toluene and the product is reacted with 2 : 6-dimethylaniline to give o -diethylamino - 2 : 6 - dimethylacetanilide; (5) sodium b -dimethylaminopropionate is reacted with benzoyl chloride in trichloro ethylene and the product is reacted with 2 : 6-dimethylaniline to give b - dimethylamino - 2 : 6 - dimethylpropionanilide; and (6) sodium 1-piperidylacetate is treated with benzoyl chloride in trichloroethylene and the product is treated with o-toluidine to give a -1-piperidyl-o-acetotoluidide.