تفاعل #516367

معادلة التفاعل

4-piperidone hydrochloride hydrate

phosphoric acid

2-Phenylindole

EtOAc

→

title compound

المردود 73.0%

3-(1,2,3,6-Tetrahydropyridin-4-yl)-2-phenyl-1H-indole

المردود 73.0%

المذيبات

AcOH

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with EtOAc (3×200 ml)
2. 2
   غسيلThe combined organic layers were washed with water and brine
3. 3
   أخرىdried
4. 4
   أخرىevaporated in vacuo
5. 5
   أخرىto give a pale yellow solid
6. 6
   أخرىthe solid collected
7. 7
   غسيلwashed with EtOAc
8. 8
   أخرىdried

الإجراء التجريبي

2-Phenylindole (25 g, 130 mmol) was stirred at 80° C. in AcOH (200 ml), and 4-piperidone hydrochloride hydrate (50 g, 376 mmol) and 1M phosphoric acid (100 ml) added. After a further 6 h, the mixture was poured into ice/ammonia, and extracted with EtOAc (3×200 ml). The combined organic layers were washed with water and brine, dried, and evaporated in vacuo to give a pale yellow solid. This was suspended in boiling EtOAc (200 ml), cooled to room temperature overnight, and the solid collected, washed with EtOAc and dried to give the title compound (26 g, 73%) as a pale yellow solid; δH (360 MHz, d6-DMSO) 2.00-2.10 (2H, m, NCH2CH2), 2.89 (2H, t, J 5, NCH2CH2), 3.40-3.45 (2H, m, NCH2CH), 5.78 (1H, br s, NCH2CH), 7.00 (1H, t, J 7, indole-H), 7.08 (1H, t, J 7, indole-H), 7.20-7.50 (5H, m, ArH), 7.69 (2H, d, J 7, ArH), 11.3 (1H, br s, indole NH); m/z (ES+) 275 (M++H).

المصدر