反応 #516367

反応方程式

4-piperidone hydrochloride hydrate

phosphoric acid

2-Phenylindole

EtOAc

→

title compound

収率 73.0%

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

収率 73.0%

溶媒

AcOH

反応条件

後処理

1. 1
   抽出extracted with EtOAc (3×200 ml)
2. 2
   洗浄The combined organic layers were washed with water and brine
3. 3
   その他dried
4. 4
   その他evaporated in vacuo
5. 5
   その他to give a pale yellow solid
6. 6
   その他the solid collected
7. 7
   洗浄washed with EtOAc
8. 8
   その他dried

実験手順

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).

出典