Acetic Acid → 2-Imino-4-methylpiperidine acetate

Participants

Reaction Steps

2-Amino-4-methylpyridine (1.56 g; 15 mmoles) and 5% rhodium on carbon (0.51 g, wet, Degussa type G10) in glacial acetic acid (30 mL) were shaken on a Parr hydrogenation apparatus at 55 psi of hydrogen overnight. The catalyst was removed by filtration and the filtrate was diluted with water to 250 mL, and lyophilized to yield a light tan powder. The powder was recrystallized from warm ethanol/ether to give 0.3 g of white solid. mp 181°-182° C. A second crop of white solid was obtained (0.85 g; mp 180°-182° C.). MH+=113; 1H NMR (D2O): δ3.32-3.16 (m, 2H); 2.54-2.46 (m, 1H); 2.10-2.00 (m, 1H); 1.80-1.70 (m, 2H); 1.74 (s, 3H); 1.32-1.25 (m, 1H); 0.87 (d, J=6.6 Hz, 3H).

Provenance & Evidence