Hydrochloric Acid → HCID 86670532, compound

Participants

Reaction Steps

To a dichloromethane (50 mL) solution of 6-(4-hydroxypiperidin-1-yl)pyridine-3-carbonitrile (3.19 g, 15.7 mmol) and triethylamine (9.0 mL, 65 mmol) was added 4-(trifluoromethyl)benzenesulfonyl chloride (4.31 g, 17.6 mmol). 4-(Dimethylamino)pyridine (0.19 g, 1.6 mmol) was then added, and the reaction mixture was stirred at room temperature for 2 hours. Diethyl ether (100 mL) was added, followed by 1.0 M hydrochloric acid (70 ml, 70.0 mmol). The organic layer was separated and washed with 1.0 M hydrochloric acid (2×50 mL), saturated brine, dried (magnesium sulfate) to afford the title compound as a solid. This crude product was used in the subsequent step without further purification. 1H NMR (500 MHz, CDCl3) δ 8.39 (d, J=2.3 Hz, 1H), 8.08 (d, J=8.3 Hz, 2H), 7.85 (d, J=8.2 Hz, 2H), 7.61 (dd, J=9.0, 2.4 Hz, 1H), 6.61 (d, J=9.1 Hz, 1H), 4.94-4.88 (m, 1H), 3.87 (ddd, J=13.7, 7.9, 3.8 Hz, 2H), 3.62 (ddd, J=13.8, 7.3, 3.9 Hz, 2H), 1.97-1.90 (m, 2H), 1.89-1.81 (m, 2H); LC-MS: m/z 412.0 (M+H).

Provenance & Evidence