反应详情

To a stirred solution of N-(1-[2-chloro-9,10-dihydro-9,10-methanoanthracen-9-ylmethyl]-4-piperidyl)-trans-3-(3-pyridyl)propenamide (170 mg, 0.36 mmol) in ethanol (5 mL) was added 10% palladium on carbon (17 mg). This mixture was hydrogenated at 1 atmospheric pressure for 18 h. The reaction was filtered through diatomaceous earth. The filtrate as concentrated and the resulting residue was chromatographed over silica gel (eluant: 95:5 methylene chloride:methanol) to give a white foam. This material was dissolved in a cold (ice bath) solution of ether:chloroform (3:1, v/v, 15 mL) and treated with gaseous hydrochloric acid to afford the title compound as a white solid (100 mg, 52%), mp 220.0°-3.0° C.; (MS(CI): 472 (M+H); NNR (300 MHz,DMSO-d6): 1.65-2.06(m, 4H), 2.46(t, 1.70H, J=7.5 Hz), 2.59(t, 0.3H, J=7.5 Hz), 2.73(m, 2H), 2.87-3.03(m, 2H), 3.17-3.66(m, 3H), 3.78(br m, 0.85H), 3.96(m, 0.15H), 4.18-4.40(m, 2H), 4.48(s, 1H), 6.95-7.10(m, 3H), 7.27-7.42(m, 3H), 7.48(s, 1H), 7.59-7.71(m, 1H), 8.02(d, 1H, J=7.5 Hz), 8.11(d, 1H, J=7.2 Hz), 8.35(br s, - 0.15H), 8.54-8.65(m, 2H), 8.68(br s, - 0.85H), 9.70(br s, 0.15H), 9.96-10.08(br s, 0.85H).

1. filtrationThe reaction was filtered through diatomaceous earth
2. concentrationThe filtrate as concentrated
3. customthe resulting residue was chromatographed over silica gel (eluant: 95:5 methylene chloride:methanol)
4. customto give a white foam