Pharmacologically active benzo[b]thiophen derivatives. Part X. 2-(5- and 7-Hydroxy-3-benzo[b]thienyl)ethylamines and related compounds

Abstract

Some 2- and 3-dialkylaminomethyl-5-methoxybenzo[b]thiophens have been prepared from the appropriate bromomethyl compound and secondary amines. The bromomethyl compounds have been converted into the corresponding nitriles and reduced to 2-(5-methoxy-2- or -3-benzo[b]thienyl)ethylamine. 2-(5-Hydroxy-3-benzo[b]thienyl)ethylamine has been prepared from 5-nitro-3-benzo[b]thienylacetic acid and isolated and characterised as its maleate. The isomeric 7-hydroxy-compound has been prepared from 7-hydroxy-3-methylbenzo[b]-thiophen via the nitrile and has been isolated as its hydrochloride.