Benzyl mercaptan → HCID 18919778, compound

Participants

Reaction Steps

0.8 g (0.02 mol) of sodium hydride (60% dispersion in oil) was washed three times with hexane and suspended in 20 ml of THF. 2.24 ml (0.019 mol) of benzyl mercaptan in 12 ml of THF were added dropwise at 0°. The mixture was stirred at room temperature for 15 min. and subsequently 0.95 g (0.0037 mol) of 1-benzylpiperidin-4-yl methanesulfonate in 10 ml of THF was added dropwise. The reaction mixture was boiled at reflux for 22 hrs. and then poured into 200 ml of 2N aqueous NaOH. The inorganic phase was extracted with ether and the combined organic phases were washed with 2N aqueous NaOH and dried over magnesium sulfate. The residue was chromatographed on silica gel with ethyl acetate/hexane (1:3→1:1) as the eluent. 0.444 g (40%) of 1-benzyl-4-benzylsulfanylpiperidine was obtained as a yellow oil. MS: me/e (% basic peak)=297 (C19H23 NS+, 1.4), 206 (62), 174 (23), 91 (199).

Provenance & Evidence