N-Methylcyclohexylamine → 4-amino-2-chloro-N-cyclohexyl-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 15 gm of N-(4-amino-2-chloro-benzoyl)-imidazole (m.p. 122°-127° C) and 150 ml of N-methyl-cyclohexylamine was stirred at 130° C for 4 hours. Subsequently, chloroform was added to the reaction mixture, and the resulting mixture was extracted twice with 300 ml of water. The organic phase was dried with sodium sulfate and evaporated. The oily residue was purified by chromatography on a silicagel column with chloroform/methanol (6:1), and the combined eluate fractions containing the desired product were evaporated. The residue was crystallized from isopropanol, yielding 4-amino-2-chloro-N-cyclohexyl-N-methyl-benzoic acid amide, m.p. 166°-170° C.

Provenance & Evidence