GB624016A - Manufacture of tertiary and quaternary trisubstituted acetic acid aminoalkyl esters - Google Patents

Abstract

Tertiary and quaternary aminoalkyl esters of a -phenyl-a -oxyacetic acids which contain as a further substituent in the a -position an alkyl radical of at least 4 carbon atoms are prepared by reacting the appropriate a -substituted-a -phenyl-a -oxyacetic acid or a reactive derivative thereof with a tertiary or quaternary amino alkanol, or by reacting a reactive ester of a tertiary or quaternary amino alkanol with the acid or a salt thereof. The products, when they contain a tertiary amino group, may be converted into their quaternary salts. In an example, a - phenyl - a - amyl - a - oxyacetic acid reacts with chlorethyldiethylamine in ethyl acetate in the presence of potassium carbonate giving a - phenyl - a - amyl - a - oxyacetic acid diethylaminoethyl ester, which may be converted into its hydrochloride. Similarly, the dimethylaminoethyl ester may be prepared, which may be converted into its ethyl bromide or methyl chloride. a -Phenyl-a -butyl-a -oxyacetic acid and a -phenyl-a -hexyl-a -oxyacetic acid react similarly. Instead of the ethylaminoethyl and methylaminoethyl esters, the corresponding piperidinoethyl, diethylaminobutyl, diallylaminoethyl, morpholinoethyl and methyl-propylaminoethyl esters and quaternary salts thereof may be prepared. Trisubstituted acetic acids, e.g. phenyl-amyl-oxyacetic acid and phenyl-butyl-oxyacetic acid, used as starting materials are obtained by reacting a benzoyl-formic acid ester with an organo-metallic compound to convert the keto group into a group of the formula <FORM:0624016/IV (b)/1> where R is an aliphatic hydrocarbon radical containing at least 4 carbon atoms, and hydrolysing the product to obtain the free acid. The Specification as open to inspection under Sect. 91 comprises also the use as starting materials of amino alcohols in general. This subject-matter does not appear in the Specification as accepted.