2-Piperidone → HCID 20763734, compound

Participants

Reaction Steps

To a solution of 4-fluorobenzyl bromide (15 g, 79 mmol) and 2-piperidinone (8.4 g, 85 mmol) in DMF (150 mL) was added sodium hydride (3.6 g of a 60% suspension in mineral oil, 90 mmol) in portions over a period of 20 min. The mixture was stirred at ambient temperature for 18 hours. The solvent was removed under vacuum and the residue was partitioned between EtOAc and water. The organic extract was washed with brine, dried over MgSO4, filtered, and concentrated under vacuum. The residual oil was purified using silica gel column chromatography eluting with 50%-70% ethyl acetate in hexanes. The appropriate fractions were combined and concentrated to afford the title compound as white solid. 1H NMR (400 MHz, CDCl3) δ 7.23 (dd, J=8.7; 5.4 Hz, 2H), 7.00 (t, J=8.7 Hz, 2H), 4.56 (s, 2H), 3.18 (t, J=6 Hz, 2H), 2.46 (t, J=6 Hz, 2H), 1.79 (m, 4H).

Provenance & Evidence