Benzeneacetic acid, 3,4-dimethoxy-, methyl ester → N-(3,4-dimethoxybenzyl)-2-(3-methylphenyl) ethylamine

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Reaction Steps

A solution of methyl 3,4-dimethoxyphenylacetate (18.5 g, 0.088 mole) and 2-(3-methylphenyl) ethylamine was heated at 180° for 1 h. The crude amide was dissolved in 50 ml of methanol and precipitated as fine needles with 150 ml of hexane to give the title compound (20.4 g, 74%). The mother liquor deposited more material which was recrystallized from toluene (charcoal) to give an additional 4.7 g (17%) of amide. The total yield of N-(3,4-dimethoxyphenylacetyl)-2-(3-methylphenyl) ethylamine, mp 101°-102°, was 91%.

Provenance & Evidence