HCID 67272021, compound → (5-Aminomethyl-2-{[(4-tert-butyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-phenyl)-methanol

Participants

Reaction Steps

To a solution of 4-{[(4-tert-butyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-3-hydroxymethyl-benzonitrile (0.153 g, 0.34 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, 90:5:5, v/v/v) afforded (5-aminomethyl-2-{[(4-tert-butyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-phenyl)-methanol as a pale yellow oil (0.085 g, 56%). 1H NMR (CDCl3) δ 1.39 (s, 9H), 1.54 (m, 1H), 1.77 (br s, 2H), 1.82 (m, 1H), 1.99 (m, 1H), 2.22 (m, 1H), 2.68 (m, 1H), 2.79 (m, 1H), 3.51 (d, 1H, J=12.0 Hz), 3.63 (dd, 2H, J=13.5, 4.5 Hz), 3.80 (s, 2H), 3.87 (m, 1H), 4.06 (d, 2H, J=12.0 Hz), 4.41 (d, 1H, J=12.0 Hz), 7.05 (dd, 1H, J=7.5, 3.0 Hz), 7.15-7.27 (m, 4H), 7.32 (d, 1H, J=9.0 Hz), 7.89 (s, 1H), 8.35 (d, 1H, J=6.0 Hz), 8.50 (d, 1H, J=3.0 Hz).

Provenance & Evidence