Benzoyl chloride → N-Benzoylbenzylamine

Participants

Reaction Conditions

Reaction Steps

To a mixture of benzylamine (75.0 g, 0.700 mol), THF (300 mL) and triethylamine (70.8 g, 134 g, 0.700 mol) was added dropwise benzoyl chloride (98.4 g, 0.700 mol) at 2° C. or lower, and the mixture was allowed to warm, and stirred at 12-35° C. for 3 hr. The progress of the reaction was confirmed by TLC (eluent: toluene/ethyl acetate (4:1)). To the reaction mixture was added water (165 mL) at 16° C. or lower, the mixture was extracted with ethyl acetate (60 mL), and the aqueous layer was extracted with ethyl acetate (150 mL). The combined organic layers were washed successively with 5% aqueous citric acid solution (50 mL×2) and 20% brine (75 mL×3), and dried over magnesium sulfate (20 g). The silica gel (12 g) was added to the solution, and the mixture was filtered through silica gel. The filtrate was concentrated under reduced pressure at 40° C. until the beginning of the precipitation. To the concentrate (263 g) was added ethyl acetate (41.5 g), and the resulting solid was dissolved at 60° C. The solution was cooled over 2 hr to 20° C., and ethyl acetate (40 mL) was added thereto. Then, the mixture was cooled to 5° C., and the resulting crystals were collected by filtration, and washed with cold ethyl acetate (75 mL). The obtained crystals were dried under reduced pressure at 40° C. to give N-benzylbenzamide (116 g, yield 78.5%) as white crystals.

Provenance & Evidence