2-Nitro-5-(piperidin-1-yl)pyridine → 5-(Piperidin-1-yl)pyridin-2-amine

Participants

Reaction Steps

6′-Nitro-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl (4.69 g, 22.6 mmol) was dissolved in THF (100 mL) to which Raney Nickel (1.08 g) was added. The reaction was shaken under a hydrogen atmosphere (50 psi) for 4 hours. The catalyst was removed by filtration and the solvent evaporated to give 3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-6′-ylamine as a purple solid (4.86 g, 85.7%). 1H NMR δ (400 MHz, CDCl3) 7.76 (d, J=2.4 Hz, 1H), 7.19 (dd, J=2.9, 8.8 Hz, 1H), 6.47 (dd, J=0.7, 8.8 Hz, 1H), 4.18 (s, 2H), 2.97 (m, 4H), 1.71 (m, 4H), 1.53 (m, 2H).

Provenance & Evidence