반응 #516367

반응 방정식

4-piperidone hydrochloride hydrate

phosphoric acid

2-Phenylindole

EtOAc

→

title compound

수율 73.0%

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

수율 73.0%

용매

AcOH

반응 조건

후처리

1. 1
   추출extracted with EtOAc (3×200 ml)
2. 2
   세척The combined organic layers were washed with water and brine
3. 3
   기타dried
4. 4
   기타evaporated in vacuo
5. 5
   기타to give a pale yellow solid
6. 6
   기타the solid collected
7. 7
   세척washed with EtOAc
8. 8
   기타dried

실험 절차

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).

출처