C(N(S(F)(F)[F:7])CC)C.[CH2:10]([N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][CH:18]1[CH2:30]O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.[OH-].[Na+]>ClCCl>[CH2:10]([N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][CH:18]1[CH2:30][F:7])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1To 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.
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