4-Toluenesulfonyl chloride → (1-Benzylpiperidin-3-yl)methyl 4-methylbenzenesulfonate

Participants

Reaction Steps

To a solution of (1-benzylpiperidin-3-yl)methanol (820 mg) and triethylamine (0.84 mL) in dichloromethane (10 mL) was added para-toluenesulfonyl chloride (846 mg). The solution was stirred overnight at room temperature. The mixture was partitioned between dichloromethane and water. The layers were separated and the organic layer was dried over sodium sulfate and evaporated. The residue was purified by silica column chromatography, eluting with a gradient of 0 to 50% ethyl acetate in hexane to give the title compound as a colourless oil (1.15 g, 80%).

Provenance & Evidence