GB799780A - New n-alkyl-alkyl-piperidine-ª‡-monocarboxylic acid amides and n-alkyl-alkyl-pyrrolidine-ª‡-monocarboxylic acid amides - Google Patents

Abstract

The invention comprises N-alkyl-alkyl-piperidine - a - monocarboxylic acid amides and N-alkyl - alkyl - pyrrolidine - a - monocarboxylic acid amides of the formul\mg <FORM:0799780/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 of such amides. The compounds are prepared by reacting the chloride of a 2-chloro-6-amino-caproic acid having an alkyl substitutent at one or two of the 3-, 4-, 5- and 6-positions or the chloride of a 2 - chloro - 5 - amino - valeric acid having an alkyl substitutent at one or two of the 3-, 4- and 5-positions, preferably in the form of the hydrochloride, with aniline or an appropriately substituted aniline to form the corresponding amide of the acid, then effecting ring closure under the action of sodium hydroxide, and finally alkylating the nuclear nitrogen. 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 - 4 - methyl - pyrrolidine - 2 - carboxylic acid - 2 - ethoxy - anilide, N - ethyl-4 - methyl - pyrrolidine - 2 - carboxy - 2 - ethyl-anilide, N - n - butyl - 5 - ethyl - pipecolyl - 2 - chloro - 6 - methyl - anilide and N - methyl-4-methyl-pipecolyl-2 : 6-xylidide.