Agomelatine → N-(2-(7-hydroxy-1-naphthyl)ethyl)acetamide

Participants

Reaction Steps

Under an inert atmosphere, 27.5 mmol of boron tribromide/dimethyl sulphide complex are dissolved in 100 ml of dichloromethane and stirred for 15 minutes at ambient temperature. A solution of 13.7 mmol of N-[2-(7-methoxy-1-naphthyl)ethyl]acetamide in 50 ml of dichloromethane is added, and the reaction mixture is heated at reflux for 30 hours. After cooling, the reaction mixture is cautiously hydrolysed and the dichloromethane is evaporated off. The mixture is then extracted with ethyl acetate and the combined organic phases are washed with an aqueous 1M potassium hydrogen carbonate solution. The organic phase is dried over magnesium sulphate and concentrated to yield the title compound. White solid.

Provenance & Evidence