Water → 1,4-Dibenzyl-2-(fluoromethyl)piperazine

Participants

Reaction Steps

To a solution of diethylaminosulfur trifluoride (1.5 ml, 12.16 mmol) in dichloromethane (10 ml) at −72° C. was added 1,4-dibenzyl-2-(hydroxymethyl)piperazine (3 g, 10.1 mmol) in dichloromethane (20 ml) over 10 minutes. The mixture was stirred for 16 h whilst warming to room temperature and treated with water (20 ml). The aqueous phase was basified to pH 9 using 4 M sodium hydroxide and the organic phase separated. The aqueous phase was extracted with dichloromethane (2×30 ml) and the combined organic layers dried with sodium sulfate and evaporated. The residue was purified by flash chromatography eluting with 20% (v/v) ethyl acetate in hexane to afford 1,4-dibenzyl-2-(fluoromethyl)piperazine (0.94 g) as a colourless oil.

Provenance & Evidence