Potassium Carbonate → 4-(p-Fluorobenzoyl)-1-(3-hydroxypropyl)piperidine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(p-fluorobenzoyl)piperidine hydrobromide (0.3 g, 1.04 mmol) in DMF (10 mL) were added 3-bromo-1-propanol (0.11 mL, 1.25 mmol) and potassium carbonate (0.29 g, 2.08 mmol). This heterogeneous solution was heated at 110° C. for 3 h then cooled at 25° C., diluted with water (100 mL) and extracted with EtOAc (3×30 mL). The collected organic phase was washed with water (2×50 mL), dried and concentrated in vacuum. The crude compound was purified by filtration on silica gel using CH2Cl2/MeOH as eluant to afford the title compound as a pale yellow solid (0.13 g, 47%). m.p. =106-108° C. 1H NMR (CDCl3): 1.55-1.68 (m, 2H), 1.68-1.95 (m, 5H), 2.05-2.2 (m, 2H), 2.642 (t, J=5.4 Hz, 2H), 3.13 (bd, J=11.7 Hz, 2H), 3.15-3.3 (m, 1H), 3.808 (t, J=4.8 Hz, 2H), 7.137 (t, J=8.4 Hz, 2H), 7.95 (dd, J=5.4 & 8.4, 2H). Anal. Calcd. for C15H20FNO2:C, 67.90; H, 7.60; N, 5.28; Found: C, 66.71; H, 7.38; N, 5.44.

Provenance & Evidence