Collection of Czechoslovak Chemical Communications - digital archive 

Abstract

Reactions of potassium salts of 2-methoxy-, 2-ethoxy- and 2-benzyloxyphenol with 2-methyl-3-dimethylaminopropyl chloride and 3-dimethylamino-2phenylpropyl chloride in boiling 2-butanone in the presence of potassium iodide gave the title compounds IV-VI which were partially demethylated by treatment with ethyl chloroformate in boiling benzene and by the following alkaline hydrolysis of the crude intermediates. In series a (3-aryloxy-2-methylpropylamines) the demethylation proceeded normally under the formation of the methylamino compounds VIIa-IXa; in series b (3-aryloxy-2-phenylpropylamines), however, the treatment with ethyl chloroformate effected a double cleavage resulting, after the alkaline hydrolysis, in N-methyl-2-phenylallylamine (XIII).The pharmacological testing did not confirm the expected thymoleptic effects of the compounds (IVa, VIIa); on the other hand, the benzyl ethers IXa and especially VIb exhibited strong antiarrhythmic activity.