Pharmacologically active benzo[b]thiophen derivatives. Part III. 2-Substituted compounds

Abstract

A number of N-(5-substituted 2-benzo[b]thenyl)ethanolamines and the corresponding N-methyl and N-ethyl derivatives have been prepared by condensation of the 5-substituted 2-chloromethylbenzo[b]thiophens with ethanolamine, N-methylethanolamine, or N-methylethanolamine, or N-ethylethanolamine. These amino-alcohols reacted with thionyl chloride in dry chloroform to give the corresponding β-chlorethylamines. 2-Acetyl-5-bromo- and -5-chlorobenzo[b]thiophen have been prepared. Bromination of these ketones, followed by condensation with several secondary amines gave keto-amines which were reduced with sodium borohydride in aqueous methanol to the corresponding amino-alcohols, some of which reacted with thionyl chloride in dry chloroform as above.