Syntheses on Ammonium Compounds of Aminoalkyl Carboxylates. II

Abstract

1) β-Haloethyl esters of carboxylic acid was formed by the reaction of a carboxylic acid with ethylenehalohydrin in carbon tetrachloride, with a few drops of sulfuric acid as a catalyst. The β-haloethyl carboxylates thereby obtained were reacted with secondary or tertiary amines and several kinds of aminoalkyl carboxylate derivatives possessing antispasmodic action were prepared. 2) In the esterification of benzilic acid with ethylenehalohydrin, only the esterification occurs when the amount of sulfuric acid catalyst is small but in the presence of a large amount of the acid, concurrent etherification was found to occur. This was utilized in preparation of β-bromoethyl O-(β'-bromoethyl) benzilate (XIV) which was reacted with a secondary or tertiary amine and some novel derivatives of aminoalkyl carboxylate were obtained. 3) Application of tertiary amines with branched alkyl chain, such as diisopropylmethylamine, to β-bromoethyl diphenylacetate (IV) failed to cause the anticipated quaternization.