Sodium Carbonate → 1-(4-Fluorobenzyl)-5,6-dihydropyridin-2-(1H)-one

Participants

Reaction Steps

To a stirred solution of 1-(4-fluorobenzyl)-3-(phenylsulfinyl)piperidin-2-one one (25 g, 74 mmol) in toluene (200 mL) was added anhydrous sodium carbonate (20 g, 190 mmol). The mixture was heated to reflux for 1.5 hours. The reaction mixture was cooled to ambient temperature and the solids were removed by filtration. The filtrate solvent was removed under vacuum and the residue was purified using silica gel column chromatography eluting with 3:1 EtOAc:hexanes. Appropriate fractions were combined and removal of the solvents under vacuum gave the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.26 (m, 2H), 7.01 (m, 2H), 6.56 (dt, J=9.9, 4.2 Hz, 1H), 6.00 (dt, J=9.7, 1.8 Hz, 1H), 4.59 (s, 2H), 3.32 (t, J=7.2 Hz, 2H), 2.33 (m, 2H).

Provenance & Evidence