Methyl 3,4-Dimethoxybenzoate → N-(3,4-Dimethoxybenzoyl)-2-(3-methylphenyl) ethylamine

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A stirred solution of 2-(3-methylphenyl) ethylamine (28.3 g, 0.21 mol) and 36.9 g of methyl 3,4-dimethoxybenzoate (36.9 g, 0.19 mol) was heated at 180° for 4 h. The crude amide was taken up in CH2Cl2 and washed with dilute HCl, dilute Na2CO3 and water. Chromatography over neutral alumina afforded 29 g (51%) of the title compound (one spot by tlc) eluted with CH2Cl2. The analytical sample showed mp 108-109° after crystallization from i-PrOH.

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