C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[CH:14]([CH2:26][OH:27])[CH2:13]1.O>C(Cl)Cl>[CH3:11][N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[CH:14]([CH:26]=[O:27])[CH2:13]1To a solution of oxalyl chloride (3.3 mL, 37.9 mmol) in methylene chloride (100 mL) cooled below −40° C. was added dimethyl sulfoxide (5.6 mL, 79 mmol) in methylene chloride (5 mL). The reaction was stirred for another 30 min at −40° C. and 1-methyl-3-hydroxymethyl-4-(3,4-dichlorophenyl)piperidine (9.0 g, 33 mmol) in methylene chloride (100 mL) was added over 15 min while keeping the temperature below −40° C. The reaction was stirred for another 30 min at this temperature and then allowed to heat to room temperature. Water (100 mL) was added and the organic phase separated off. The aqueous phase was extracted with methylene chloride (2×100 mL). The combined organic extracts were dried over magnesium sulphate and evaporated to dryness to give 10 g of the title compound.
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