Dibenzylamine → N-[4-(N,N-Dibenzylglycyl)phenyl]methanesulfonamide

Participants

Reaction Steps

4'-(2-Bromoacetyl)methanesulfonanilide (Temple, D. L. et al., J. Med. Chem., 19(5), 626-633 (1976)) (40 g) and dibenzylamine (Aldrich Chemical Co., Milwaukee, Wis. 53233) (55.2 g) were combined in acetone (550 ml) and stirred 3 hours at ambient temperature. A heavy precipitate of dibenzylamine.HBr was filtered off. The filtrate was evaporated and crystallized first from MeOH and then from 2-PrOH. This yielded the product, 4'-(2-dibenzylaminoacetyl)methanesulfonanilide (XXVI) as a crystalline solid, 42.9 g, m.p. 131°-134°, whose thin layer chromatography analysis (silica, EtOAc/hexane) and NMR indicated a single compound with the structure indicated above.

Provenance & Evidence