HCID 12972966, compound → HCID 12972966, compound

Participants

Reaction Conditions

Reaction Steps

4-Benzyl-1-(2,3-dihydroxypropyl)piperidine. A solution of 4-(4-Benzyl-piperidin-1-yl)-2,2-dimethyl-1,3-dioxolane (0.65 g) in methanolic HBr (1.0 M, 20 mL) was prepared. The solution was stirred at 25° C. for 2 h then was concentrated in vacuo. The resulting crude product was dissolved in water (50 mL), washed with ether (20 mL), made basic with saturated NaHCO3 (20 mL) and extracted with CH2Cl2 (3×30 mL). The crude compound was purified by trituration with EtOAc (5 mL) for 2 h to give the title compound as a colorless solid (0.45 g, 80%): mp 92-94oC; 1H NMR (CDCl3) δ 1.15-1.40 (m, 2H), 1.45-1.65 (m, 1H), 1.64 (bd, J=13.5 Hz, 2H), 1.92 (t, J=11.4 Hz, 1H), 2.20 (t, J=11.4 Hz, 1H), 2.30 (dd, J=3.9 and 12.3 Hz, 1H), 2.45-2.60 (m, 3H), 2.81 (bd, J=11.4 Hz, 1H), 2.98 (bd, J=11.1 Hz, 1H), 3.65-3.85 (m, 2H), 7.14 (d, J=7.2 Hz, 2H), 7.20 (d, J=6.9 Hz, 1H), 7.28 (t, J=7.2 Hz, 2 H; MS (m/z) 249, 232, 218, 188, 91. Anal. Calcd for C15H23NO2: C, 72.25; H, 9.30; N, 5.62. Found C, 72.19; H, 9.43; N, 5.75.

Provenance & Evidence