ClC1C=CC=C(C(OO)=[O:9])C=1.[N:12]1([C:18]2[C:23]([Br:24])=[CH:22][N:21]=[C:20]([CH3:25])[CH:19]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>ClCCl>[N:12]1([C:18]2[CH:19]=[C:20]([CH3:25])[N+:21]([O-:9])=[CH:22][C:23]=2[Br:24])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1m-Chloroperbenzoic acid (7.3 g) in dichloromethane (100 ml) was added dropwise to a stirred solution of 4 -piperidino-5 -bromo-2 -picoline. After 16 hours, the solution was washed with 10 % aqueous sodium carbonate, dried (K2CO3) and stripped. The residue was chromatographed (silica gel, chloroform:methanol) to give 4 -piperidino-5 -bromo-2 -picoline-N-oxide, 6.79 g, m.p. 115°-6 ° from ether.
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