4-Chlorobenzenesulfonyl chloride → 4-chloro-N-(1-(hydroxymethyl)cyclohexyl)benzenesulfonamide

Participants

Reaction Steps

4-Chlorobenzenesulfonyl chloride (6.92 g, 32.8 mmol) was added to a solution of (1-aminocyclohexyl)methanol (prepared according to Helv. Chirp. Acta, 87:90-105 (2004)) (3.53 g, 27.3 mmol) and triethylamine (4.6 mL, 32.8 mmol) in 100 mL tetrahydrofuran at room temperature. The reaction was stirred overnight and concentrated. The residue was taken up in a mixture of 100 mL ethyl acetate and 100 mL brine. The organic layer was separated, dried over sodium sulfate, and purified by flash chromatography on 120 g silica gel with 20 to 100% ethyl acetate in hexane to yield 4-chloro-N-(1-(hydroxymethyl)cyclohexyl)benzenesulfonamide (6.07 g, 73%). 1H NMR (400 MHz, CDCl3) δ ppm 7.85-7.86 (1H, m), 7.81-7.84 (1H, m), 7.47-7.49 (1H, m), 7.44-7.46 (1H, m), 4.61 (1H, s), 3.60 (2H, d, J=5.54 Hz), 2.25 (1H, t, J=5.92 Hz), 1.57-1.69 (2H, m), 1.22-1.45 (8H, m). LC/MS R.T.=2.39 min; [M+H]+=304.03; [M+Na]+=326.05; [M−H]−=301.98.

Provenance & Evidence