Water → HCID 23370160, compound

Participants

Reaction Steps

To benzyl mercaptan (17 ml, 152 mmol)in dimethylformamide at 0° C. under nitrogen was added sodium hydride (80% dispersion in mineral oil, 4.38 g, 152 mmol) the solution was stirred at room temperature for 15 minutes then cooled to 0° C. prior to adding N-Boc-(4-bromo)piperidine (10.8 g, 38 mmol). The mixture was stirred for 14 h at room temperature then poured into water (50 ml), extracted with diethyl ether (2×100 ml), the organic layers combined, dried (MgSO4), filtered, evaporated, and the crude product purified by flash column chromatography using 10% ethyl acetate in hexane to yield the product as a pale yellow oil (2.86 g); δH (CDCl3) 1.46 (9H, s, t-Bu), 1.51 and 1.87 (4H, m, 3,5-piperidinyl CH2), 2.85 and 3.91 (4H, m, 2,6-piperidinyl CH2), 2.69 (1H, m, 4-piperidinyl H), 3.77 (2H, s, SCH2), and 7.24-7.32 (5H, m, ArH).

Provenance & Evidence