反应详情

To a solution of 3-hydroxymethyl-4-{[(4-phenyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzonitrile (0.183 g, 0.40 mmol) dissolved in MeOH (8 mL) NH3 gas was bubbled for 10 minutes. A prewashed mixture of Raney Nickel (˜1 gram) was added to the nitrile and the mixture was shaken on the hydrogenator at 35 psi for 2 hours. The mixture was filtered through a sintered glass funnel containing a celite plug and the filtrate was concentrated in vacuo to a pale yellow oil. Purification by column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 87:8:5, v/v/v) afforded (5-aminomethyl-2-{[(4-phenyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-phenyl)-methanol as a colorless oil (0.036 g, 19%). 1H NMR (CDCl3) δ 1.61 (m, 1H), 1.92-2.05 (m, 2H), 2.29 (m, 1H), 2.66 (m, 1H), 2.79 (m, 1H), 3.60 (d, 1H, J=12.0 Hz), 3.68-3.81 (m, 4H), 3.93 (m, 1H), 4.08 (m, 3H), 4.49 (d, 1H), 7.01 (dd, 1H, J=7.5, 3.0 Hz), 7.16 (d, 1H, J=7.5 Hz), 7.24-7.30 (m, 3H), 7.44 (m, 2H), 7.57 (t, 2H, J=7.5 Hz), 7.92 (d, 2H, J=6.0 Hz), 8.11 (s, 1H), 8.47 (d, 1H, J=3.0 Hz), 8.50 (d, 1H, J=4.5 Hz).

1. customwas bubbled for 10 minutes
2. additionA prewashed mixture of Raney Nickel (˜1 gram)
3. additionwas added to the nitrile
4. filtrationThe mixture was filtered through a sintered glass funnel
5. additioncontaining a celite plug
6. concentrationthe filtrate was concentrated in vacuo to a pale yellow oil
7. customPurification by column chromatography on silica gel (CH2Cl2