Piperidine → 5-Nitro-2-piperidinopyridine

Participants

Reaction Conditions

Reaction Steps

To a slurry of 2-chloro-5-nitropyridine (100 g, 632 mmol) in ethanol (2000 mL) at room temperature was added piperidine (206 mL, 2.08 mol) and the mixture heated to 60° C. for 30 minutes. The cooled mixture was concentrated and the residue taken up in CH2Cl2 then washed with saturated NaHCO3 and brine. The mixture was dried (Na2SO4), filtered, and concentrated to provide the title compound as a yellow solid (130.4 g, 99% yield). 1H NMR (400 MHz, DMSO-D6) δ 8.94 (d, J=2.9, 1H), 8.17 (dd, J=9.6, 2.9, 1H), 6.93 (d, J=9.6, 1H), 3.79-3.73 (m, 4H), 1.69-1.64 (m, 2H), 1.61-1.51 (m, 4H).

Provenance & Evidence