Hydrochloric Acid → 1-[3-(1H-1,2,3-triazol-1-yl)phenyl]piperidin-4-ol

Participants

Reaction Steps

To an ethanol (18 mL) solution of 4-{[tert-butyl(dimethyl)silyl]oxy}-1-[3-(1H-1,2,3-triazol-1-yl)phenyl]piperidine (1.83 g, 5.12 mmol) was added concentrated hydrochloric acid (1030 μL, 12.5 mmol). After 6 hours, the reaction mixture was quenched with saturated aqueous sodium hydrogencarbonate solution (30 mL) and charged with ethyl acetate (30 mL). The reaction mixture was stirred vigorously for 10 minutes. The aqueous layer was extracted with more ethyl acetate (2×30 mL). The combined organic extracts were washed with brine, dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography over silica gel, eluting with hexanes/ethyl acetate, afforded the title compound as a pale yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.97 (s, 1H), 7.83 (s, 1H), 7.37 (s, 1H), 7.36 (t, J=8.1 Hz, 1H), 7.04 (d, J=8.0 Hz, 1H), 6.98 (d, J=8.5 Hz, 1H), 3.97-3.87 (m, 1H), 3.66 (dt, J=12.7, 4.7 Hz, 2H), 3.05 (ddd, J=12.7, 9.7, 3.1 Hz, 2H), 2.07-1.98 (m, 2H), 1.75-1.66 (m, 2H); LC-MS: m/z 245.2 (M+H).

Provenance & Evidence