Potassium Hydroxide → HCID 11276773, compound

Participants

Reaction Steps

N-{3-[4-(4-Chloro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-2,2,2-trifluoroacetamide (1.77 g, 5.10 mmol) and 20% aqueous KOH (25 mL) in ethanol (50 mL) were stirred at room temperature for 30 minutes. The reaction mixture was concentrated to dryness and the solids were washed with methylene chloride, dried over magnesium sulfate and concentrated to give 3-[4-(4-Chloro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-propylamine (0.82 g, 64%) as a waxy white solid. Mp. 57-58° C.; NMR CDCl3 δ 7.29-7.20 (m, 4H), 6.03 (s, 1H), 3.12 (d, J=3.3 Hz, 2H), 2.76 (t, J=6.9 Hz, 2H), 2.67 (t, J=5.6 Hz, 2H), 2.51-2.44 (m, 4H), 1.69 (p, J=7.5 Hz, 2H), 1.63 (s, 2H); 13C NMR CDCl3 δ 139.20, 133.96, 132.61, 128.36, 126.15, 122.41, 56.20, 53.36, 50.30, 40.77, 30.73, 28.01; IR(KBr) 2929, 2861, 2805, 2767, 2734, 1493, 1467, 1379, 1320, 1128, 1095, 845, 825, 800; Analysis calculated for C14H19CIN2.0.25H2O: C, 65.87; H, 7.70; N, 10.97. Found: C, 65.69; H, 7.44; N, 10.91.

Provenance & Evidence