4-(3,3''-Dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2';6',2'']terpyridin-1'-ylmethyl)-benzonitrile → 4-(3,3''-Dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2';6',2'']terpyridin-1'-ylmethyl)-benzylamine

Participants

Reaction Steps

A solution of 4-(3,3″-Dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-benzonitrile (0.122 g, 0.32 mmol) in NH3 saturated MeOH (3 mL) was treated with Raney nickel (100 mg) and placed under 50 psi H2, on a Parr shaker, for 4 hours. The mixture was filtered through Celite and the cake was washed with MeOH. The eluant was concentrated under reduced pressure. Purification of the crude material by column chromatography on silica gel (20:1:1 CH2Cl2—CH3OH—NH4OH) provided 93 mg (76%) of COMPOUND 68 as a white solid. 1H NMR (CDCl3) δ 1.44-1.57 (m, 1H), 1.66-1.72 (m, 2H), 1.90-2.11 (m, 3H), 2.34 (s, 6H), 3.51 (s, 2H), 3.71 (s, 2H), 3.98 (d, 2H J=10.5 Hz), 6.54 (d, 2H, J=7.8 Hz), 6.93 (d, 2H, J=7.8 Hz), 7.01 (dd, 2H, J=7.5, 4.8 Hz), 7.34 (d, 2H, J=7.5 Hz), 8.47 (d, 2H, J=3.9 Hz); ES-MS m/z 387 (M+H).

Provenance & Evidence