تفاعل #61157

معادلة التفاعل

4-acetylamino-piperidinium acetate

2-fluoro-1-nitrobenzene

triethylamine

→

title compound

المردود 5.0%

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

المردود 5.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر