Some o-substituted NN-dimethyl-2-halogeno-2-phenylethylamines

Abstract

A series of ortho-substituted NN-dimethyl-2-hydroxy-, 2-chloro-, and 2-bromo-2-phenylethylamine salts has been prepared for pharmacological evaluation. Bromination of 2-substituted acetophenones gave phenacyl bromides which were either condensed directly with dimethylamine, the resulting keto-amines then being reduced to the corresponding amino-alcohols, or were converted into the corresponding epoxides, which were then treated with dimethylamine to give the required amino-alcohols. Chlorination of bromination in the usual way gave the corresponding halogenoethylamines. The rates of formation and decomposition of the ethyleniminium ions formed from these halogenoethylamines have been studied and the results are compared with the behaviour of similar m- and p-substituted compounds. The results of a preliminary screening of the compounds for anti-adrenaline activity are also reported.