Abstract
The formation of [4, 5-dimethoxy-α-(3, 4-dimethoxyphenyl)-o-tolyl] acetonitrile (IV) as a by-product in the metathesis of 3, 4-dimethoxybenzyl chloride (II) with sodium cyanide in dimethyl sulfoxide or N, N-dimethylformamide is reported. The structure of IV has been established by analysis, ultraviolet spectrum, infrared spectrum, nuclear magnetic resonance spectrum, and conversion into 4, 5-dimethoxy-2-(3, 4-dimethoxybenzyl)-N, N-dimethylphenethylamine (XI) through [4, 5-dimethoxy-α-(3, 4-dimethoxyphenyl)-o-tolyl] acetic acid (VII) and 2-[4, 5-dimethoxy-α-(3, 4-dimethoxyphenyl)-o-tolyl]-N, Ndim thylacetamide (VIII). The sample of XI thus obtained was identical with the one produced by catalytic hydrogenolysis of 1-(3, 4-dimethoxypheny1)-1, 2, 3, 4-tetrahydro-6, 7-dimethoxy-2, 2-dimethylisoquinolinium chloride, which was synthesized from 1-(3, 4-dimethoxyphenyl)-1, 2, 3, 4-tetrahydro-6, 7-dimethoxy-2-methylisoquinoline (IX) by quaternization with methyl iodide and treatment of the resulting methiodide (X) with silver chloride. The reaction of benzyl chloride with sodium cyanide in dipolar aprotic solvents was found to give a small amount of 2, 3-diphenylpropionitrile (XIV) besides benzyl cyanide.
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