Reaktion #61157

Reaktionsgleichung

4-acetylamino-piperidinium acetate

2-fluoro-1-nitrobenzene

triethylamine

→

title compound

Ausbeute 5.0%

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

Ausbeute 5.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle