Triethylamine → N-Cyclohexyl-N-methyl-2-nitrobenzamide

Participants

Reaction Steps

A solution of 2-nitrobenzoyl chloride (1.0 g, 5.4 mmol) in dichloromethane (1 ml) was added dropwise to a stirred solution of cyclohexylmethylamine (0.068 g, 6 mmol), triethylamine (1.12 ml, 8 mmol) and a catalytic amount of 4-dimethylaminopyridine in dichloromethane (4 ml) at 0° C. After 1 h at 0° C., the reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with dichloromethane and washed with hydrochloric acid 1N (10 ml), sodium hydroxide 2N (10 ml) and brine (10 ml). The organic layer was dried (MgSO4) and concentrated under reduced pressure to yield N-cyclohexyl-N-methyl-2-nitrobenzamide (1.05 g, 74%) that was used in the next step without further purification.

Provenance & Evidence