Hydrogen Sulfide → HCID 86071503, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of 4-cyano-1-(4-fluorobenzyl)-4-phenylpiperidin-2-one (3.39 g, 10.9 mmol) in pyridine (77 mL) was added triethylamine (45.0 g, 0.77 mol). The reaction mixture was saturated with hydrogen sulfide gas, the reaction vessel was sealed and then brought to ambient temperature. After stirring for 24 hours, the reaction mixture was cooled (0° C.), the reaction vessel was opened, then the solvents were concentrated under vacuum. The residual material was purified using silica gel column chromatography eluting with 0-70% EtOAc in hexanes. The appropriate fractions were combined and concentrated to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 9.65 (s, 1H), 8.68 (s, 1H), 7.35 (m, 4H), 7.26 (t, J=7 Hz, 1H), 7.13 (t, J=8.3 Hz, 2H), 7.04 (t, J=8.9 Hz, 2H), 4.48 (d, J=15 Hz, 1H), 4.35 (d, J=15 Hz, 1H), 3.16 (m, 2H), 3.93 (d, J=17 Hz, 1H), 2.82 (m, 1H), 2.51 (m, 2H) ppm. ES MS M+1=343.

Provenance & Evidence