[H-].[Na+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CS(O[CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18][CH2:17]1)(=O)=O.[OH-].[Na+]>CCCCCC.C1COCC1>[C:22]([N:19]1[CH2:20][CH2:21][CH:16]([CH2:15][S:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:17][CH2:18]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
4.27 g (0.1068 mol) of sodium hydride (60% dispersion in oil) were washed twice with hexane, suspended in 160 ml of THF and treated with 10.3 ml (0.1068 mol) of thiophenol. The mixture was stirred for 15 min. and then a solution of 5.95 g (0.02 mol) of 1-benzoylpiperidin-4-yl-methyl methanesulfonate in 20 ml of THF was added. The mixture was boiled at reflux for 18 hrs. The reaction mixture was treated with 250 ml of 2N aqueous NaOH and extracted with ether. The organic phase was washed with 2N aqueous NaOH and saturated sodium chloride solution, dried over sodium sulfate and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane (1:3) as the eluent. 5.8 g (93%) of 1-benzoyl-4thio-phenoxymethylpiperidine were obtained as yellow crystals; m.p. 76°-79°.
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