Reacción #61157

Ecuación de reacción

4-acetylamino-piperidinium acetate

2-fluoro-1-nitrobenzene

triethylamine

→

title compound

Rendimiento 5.0%

N-[1-(2-Nitro-phenyl)-piperidin-4-yl]-acetamide

Rendimiento 5.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvents were removed in vacuo
2. 2
   Otrothe residue was purified by silica gel preparative TLC
3. 3
   Lavadoeluting with dichloromethane/hexane/acetonitrile (47.5/47.5/5 v:v:v)

Procedimiento

To a flask was added 4-acetylamino-piperidinium acetate (as prepared in the previous step) (800 mg, 4.00 mmol), DMF (40 mL), 2-fluoro-1-nitrobenzene (422 μL, 4.00 mmol), triethylamine (836 μL, 6.00 mmol) and the mixture stirred at RT for 17 h. The solvents were removed in vacuo and the residue was purified by silica gel preparative TLC eluting with dichloromethane/hexane/acetonitrile (47.5/47.5/5 v:v:v) yielded 55 mg (5%) of the title compound as a crystalline orange solid. 1H-NMR (400 MHz, CDCl3): δ 8.18 (m, 1H), 8.09 (br d, 1H, J=7.2 Hz), 7.45 (m, 1H), 6.88 (m, 1H), 6.67 (m, 1H), 4.38 (m, 1H), 3.86-3.74 (m, 1H), 3.32 (m, 1H), 3.07 (m, 1H), 2.14 (s, 3H), 1.67-1.52 (m, 2H).

Fuente