Cesium carbonate → HCID 11036079, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-bromobenzenethiol (1.0 g, 0.00529 mole) in DMF (10 mL) was added cesium carbonate (2.063 g, 0.0063 mole) followed by 4-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester (1.478 g, 0.00529 mole). The reaction mixture was heated at 80° C. overnight. The mixture was then diluted with water and the product was extracted with ethyl acetate. The ethyl acetate layer was washed brine solution, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was washed with hexane to afford 1.93 g (98%) of 4-(2-bromo-phenylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester. LCMS: 372.06 (M+1)+, 92.78%. A solution of 4-(2-bromo-phenylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester (1.93 g, 0.0052 mole) in dioxane.HCl (3 mL), was stirred at ambient temperature for 30 minutes. The reaction mixture was then concentrated under reduced pressure and the resulting residue was washed with hexane twice to afford 1.38 g (99%) of 4-(2-bromo-phenylsulfanyl)-piperidine hydrochloride. 1H NMR (DMSO-d6): δ 9.1-8.9 (bs, 1H), 7.7-7.64 (d, 1H), 7.56-7.52 (d, 1H), 7.46-7.36 (t, 1H), 7.24-7.16 (t, 1H), 3.7-3.6 (m, 1H), 3.34-3.2 (bd, 3H), 3.1-2.94 (q, 2H), 2.16-2.04 (d, 2H), 1.84-1.66 (q, 2H).

Provenance & Evidence