4-(3,3''-dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2'; 6',2'']terpyridin-1'-ylmethyl)-3-hydroxymethyl-benzonitrile → [5-aminomethyl-2-(3,3''-dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2'; 6',2'']-terpyridin-1'-ylmethyl)-phenyl]-methanol

Participants

Reaction Steps

To a solution of 4-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-3-hydroxymethyl-benzonitrile (0.610 g, 1.48 mmol) dissolved in MeOH (12 mL) ammonia gas was bubbled for 10 minutes. A pre-washed mixture of Raney Nickel (˜1.5 grams) was added to the nitrile and the mixture was shaken on the hydrogenator at 45 psi for 2.5 hours. The mixture was filtered through a sintered glass funnel containing a celite plug and the filtrated was concentrated in vacuo to a green foam. Purification by column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 87:8:5, v/v/v) afforded [5-aminomethyl-2-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]-terpyridin-1′-ylmethyl)-phenyl]-methanol as a white foam (0.540 g, 88%). 1H NMR (CDCl3) δ 1.25 (br s, 1H), 1.62-1.72 (m, 3H), 2.03 (m, 1H), 2.32 (m, 2H), 2.49 (s, 6H), 2.81 (br s, 1H), 3.55 (s, 2H), 3.62 (s, 1H), 4.01 (d, 2H, J=9.0 Hz), 4.34 (s, 2H), 5.18 (br s, 1H), 6.59 (d, 1H, J=9.0 Hz), 6.72 (d, 1H, J=9.0 Hz), 6.83 (m, 3H), 7.23 (d, 2H, J=9.0 Hz), 8.22 (d, 2H, J=3.0 Hz).

Provenance & Evidence