Methylamine → 3-{4-[(3,4-Difluorophenyl)methoxy]phenyl}-N-methylprop-2-enamide

Participants

Reaction Conditions

Reaction Steps

500 mg (1.72 mmol) 3-[4-(3,4-difluoro-benzyloxy)-phenyl]-acrylic acid is suspended in 5 ml dichloromethane. 0.62 ml (8.6 mmol) thionyl chloride is added and the reaction mixture heated overnight to 45° C. Concentration leaves a yellowish tar which is dissolved again in 10 ml dichloromethane and treated with 1.1 ml of a 33% solution of methylamine in ethanol. After heating at 45° C. for 3 hours, the reaction mixture is filtered and the filtrate concentrated. Chromatography (silica gel, dichloromethane/methanol) yields 136 mg (26%) of a colorless solid. MS: m/e=304.1 (M++H).

Provenance & Evidence