p-Fluoronitrobenzene → Ethyl 1-(4-nitrophenyl)piperidine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

In a solution of 1-fluoro-4-nitro benzene (3.00 g, 21.3 mmol) in DMSO (30 mL) was added ethyl piperidine-4-carboxylate (5.01 g, 31.9 mmol) and K2CO3 (5.87 g, 42.5 mmol). The resulting mixture was stirred at 100° C. for 8 h. After cooling to rt, the reaction was quenched with H2O (70 mL). The resulting mixture was extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/petroleum ether (1:2 v/v) to obtain compound 18a as a yellow solid (5.00 g, 80% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C14H18N2O4: 279.1 (M+H). Found 279.1.

Provenance & Evidence