Methyl 3,4,5-trimethoxybenzoate → N-(3,4,5-Trimethoxybenzoyl)-2-(3-methylphenyl) ethylamine

Participants

Reaction Steps

A solution of methyl 3,4,5-trimethoxybenzoate (31.1 g, 0.138 mol) and 2-(3-methylphenyl)ethylamine (18.6 g, 0.138 mol) was heated at 180° for 6 h. The dark reaction mixture was taken up in methylene chloride and washed with dilute HCl. The solvent was evaporated and the residue was chromatographed on 150 g of neutral alumina. Elution with methyl chloride/hexane (3:1) removed some by-products and elution with methylene chloride gave nearly pure amide F1 which was recrystallized from i-PrOH to give pure F1 (5.2 g, 11%), mp 105-108°.

Provenance & Evidence