(3,4-Dimethoxyphenyl)acetic acid → N-(3,4-Dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide

Participants

Reaction Steps

A dry dichloromethane solution (1000 ml) of 3,4-dimethoxyphenylacetyl chloride prepared from 325 g of 3,4-dimethoxyphenylacetic acid and 300 ml of thionyl chloride was slowly added to a two-phase solvent consisting of 300 g of 3,4-dimethoxyphenethylamine, 850 ml of 2N sodium hydroxide, and 2000 ml of dichloromethane while stirring under ice-cooling. Chloroform was added to the mixture to dissolve the precipitated solid. The aqueous layer was removed, and the organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution, dried, and the solvent was evaporated. To the residue was added methanol, the mixture was heated and allowed to cool, and the thus precipitated crystal was collected by filtration to yield 570 g of the title compound.

Provenance & Evidence