Dimethylformamide → HCID 71226132, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added ethyl 3-methylpiperidine-3-carboxylate (2.040 g, 11.91 mmol), 1-fluoro-4-nitrobenzene (1.765 g, 12.51 mmol), DMF (20 ml) and K2CO3 (2.140 g, 15.49 mmol). The reaction was stirred at 65° C. for 6 hrs. After this time, the reaction was diluted with EtOAc. The resulting solution was washed with water (2×) and saturated aqueous NaCl. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-30% EtOAc/Hex to give product, ethyl 3-methyl-1-(4-nitrophenyl)piperidine-3-carboxylate (2.922 g, 9.90 mmol, 83% yield) as a yellow oily residue. Anal. Calcd. for C15H20N2O4 m/z 292.3, found: 293.2 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 8.10 (d, J=9.34 Hz, 2 H), 6.87 (d, J=9.34 Hz, 2 H,) 4.18 (d, J=13.19 Hz, 1 H), 4.11 (q, J=7.15 Hz, 2 H), 3.80-3.58 (m, 1 H), 3.00 (s, 1 H), 2.90 (d, J=13.19 Hz, 1 H), 2.40-2.23 (m, 1 H), 1.75 (dd, J=8.52, 4.12 Hz, 2 H), 1.42 (s, 1 H), 1.26-1.14 (m, 6 H).

Provenance & Evidence