Sodium methanethiolate → HCID 22622431, compound

Participants

Reaction Steps

Sodium thiomethoxide (0.220 g) tetra-n-butylammonium bromide (0.100 g) and tert-butyl 4-(2-chloromethylphenyl)piperidinecarbamate (0.867 g) were combined in acetone (20 mL) under nitrogen and stirred for 6 h, then heated under reflux for 90 min. The reaction was diluted with aqueous sodium bicarbonate and diethyl ether. The organic phase was dried and evaporated and the residue purified by chromatography (6:1 hexanes:ethyl acetate) to give tert-butyl 4-(2-methylthiomethylphenyl)piperidinecarbamate (0.471 g) as a yellow oil. MS: m/z222 (M-Boc). 1H NMR (CDCl3) δ 7.18 (m, 4H, Ar—H), 3.68 (s, 2H, Ar—CH2—S), 3.04 (m, 1H), 2.80 (m,3H), 2.04 (s, 3H, S—CH3), 1.70 (m, 5H), 1.49 (s, 9H). This material was N-deprotected with HCl according to the conditions described for Example 21d to afford 4-(2-methylthiomethylphenyl)piperidine. 1H NMR (CDC13) δ 7.30 (m, 4H, Ar—H), 3.77 (s, 2H), 3.63 (m, 2H), 3.10 (m, 3H), 2.25 (m, 2H), 2.04 (s, 3H, S—CH3), 1.95 (m, 2H).

Provenance & Evidence