Benzene → 1-Benzylindole

Participants

Reaction Steps

Indole (1.17 g, 0.01 mol) was added to a mixture of benzyl chloride (1.90 g, 0.015 mol), 50% aqueous sodium hydroxide solution (5 ml), benzene (10 ml) and 0.5 mmol of compound 1. The mixture was stirred at 60°-70° C. for 5 hours, then cooled to room temperature and diluted with water (10 ml). The organic layer was separated, washed with diluted hydrochloric acid, water and dried over anhydrous magnesium sulphate. The solvent and excess of benzyl chloride were removed under vacuo and the residue was chromatographed on silica gel using n-hexane to give the N-benzylindole (70%), m.p.: 43°-45° C.

Provenance & Evidence