4-Methylmorpholine → Ethyl 1-(pyridin-4-yl)piperidine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

Ethyl isonipecotate (6.0 g 38.66 mmol), 4-chloropyridine hydrochloride (5.9 g, 38.66 mmol) and N-methylmorpholine (9.3 g mL, 85.00 mmol), were dissolved in N-methylpyrrolidine (50 mL) and the resulting solution was heated at 100° C. for 48 h. The solution was concentrated in vacuo and the residue was dissolved in EtOAc and washed with water and brine (2×100 mL), then dried (Na2SO4) and evaporated. The resulting residue was purified by flash chromatography (5% MeOH/CHCl3) to afford 33-1 as a crystalline solid. 1H NMR (CDCl3) δ 8.21 (d, J=6.8 Hz, 2H), 6.78 (d, J=6.8 Hz, 2H), 4.18 (q, J=7.0 Hz, 2H), 3.85 (m, 2H), 3.10 (m, 2H), 2.61 (m, 1H), 2.05 (m, 2H), 1.85 (m, 2H), 1.23 (t, J=7.0 Hz, 3H). ##STR164## 4-Pyridylpiperidin-4-ylcarboxylic acid (33-2)

Provenance & Evidence