Synthesis of trimethylsilylphenethylamines

Abstract

o-,m-, and p-Trimethylsilylphenethylamines were obtained by lithium aluminium hydride reduction of the corresponding nitriles. α-Alkylation of p-trimethylsilylbenzyl cyanide, followed by reduction, gave 2-p-trimethylsilyl-phenylpropylamine. o-, m-, and p-Trimethylsilylphenylacetic acids were prepared by alkaline hydrolysis of the corresponding nitriles. Dimethyl-p-trimethylsilylphenethylamine was synthesised from p-trimethylsilylphenylacetic acid which was reduced to the alcohol, converted into the alkyl chloride, and aminated with dimethylamine. DL-2-Amino-1-p-trimethylsilylphenylpropane, a silicon analogue of amphetamine, was synthesised from p-trimethylsilylbenzyl alcohol which was converted into the benzyl chloride. The derived Grignard reagent was then treated with acetonitrile, followed by reduction with lithium aluminium hydride.