1-Benzyl-4-piperidone → HCID 58772035, compound

Participants

Reaction Steps

To a solution of 2-bromo-4-chloro-1-methoxybenzene (51 g, 0.23 mol) in THF (500 mL) was added dropwise n-BuLi (2.5 M in hexane, 138 mL, 0.345 mol) at −78° C. at nitrogen atmosphere. After being stirred at this temperature for 1 h, 1-benzyl-piperidin-4-one (42 g, 0.22 mol) was added dropwise. After addition, the mixture was stirred at −78° C. for 1 h, and then warmed to room temperature. The reaction was quenched with NH4Cl (Sat. aq., 300 mL), and the separated aqueous layer was extracted with ethyl acetate (150 mL×3). The combined organic layer was washed with water and brine, dried over Na2SO4, concentrated to dryness. The residue was purified by silica gel column to obtain 1-benzyl-4-(5-chloro-2-methoxy-phenyl)-piperidin-4-ol 4b as white powder product. 1H NMR (CDCl3): δ 7.37-7.24 (m, 6H), 7.21 (q, J1=8.8 Hz, J2=2.8 Hz, 1H), 6.85 (d, J=8.8 Hz, 1H), 3.88 (s, 3H), 3.80 (s, 1H), 3.59 (s, 2, H), 2.77-2.74 (m, 2, H), 2.59-2.54 (t, 2H), 2.13-2.06 (m, 2H), 2.00-1.96 (m, 2H).

Provenance & Evidence