Cesium carbonate → 4-chloro-N-(4-cyanobenzyl)-N-(trans-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide

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Reaction Steps

A solution of 4-chloro-N-(trans-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (126 mg, 0.39 mmol), cesium carbonate (254 mg, 0.78 mmol), and 4-(bromomethyl)benzonitrile (92 mg, 0.47 mmol) was stirred in 2 mL dimethylformamide for 1.5 h. The reaction was partitioned between 25 mL diethyl ether and 25 mL 0.1 M HCl, concentrated and purified by flash chromatography on 40 g silica gel with 0 to 70% ethyl acetate in hexane to yield 4-chloro-N-(4-cyanobenzyl)-N-(trans-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (152 mg, 90%). 1H NMR (400 MHz, CDCl3) δ ppm 7.73 (2H, d, J=8.31 Hz), 7.60-7.65 (2H, m), 7.54 (2H, d, J=8.31 Hz), 7.50 (2H, d, J=8.56 Hz), 4.65 (1H, d, J=16.12 Hz), 4.01 (1H, d, J=16.12 Hz), 3.76-3.88 (1H, m), 3.61-3.72 (1H, m), 3.28-3.41 (1H, m), 2.18 (1H, br. s.), 1.44-1.63 (5H, m), 1.11-1.40 (6H, m). LC/MS R.T.=2.76 min; [M+H]+=433.14. HRMS [M+H]+ calc'd 433.1353, found 433.1352.

Provenance & Evidence