Thionyl chloride (0.113 mL; 1.55 mmol) was added to a mixture of 3-benzylbenzoic acid (0.110 g; 0.518 mmol) in chloroform (10 mL). The reaction mixture was stirred at 65° C. for 18 hours and evaporated to dryness. The resulting residue was dissolved in chloroform (6 mL) and the solution is cooled to 0° C. A solution of 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.110 g; 0.466 mmol) and triethylamine (0.363 mL; 2.59 mmol) in chloroform (6 ml) was then added and the mixture was stirred for 30 minutes at room temperature. The volatiles were removed under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluent 1 to 20% ethyl acetate in dichloromethane) to furnish 0.154 g (76%) of 3-benzyl-N-(2-(5-chloro-1H-indol-3-yl)ethyl)benzamide as a white solid.
