Reaktion #516367

Reaktionsgleichung

4-piperidone hydrochloride hydrate

phosphoric acid

2-Phenylindole

EtOAc

→

title compound

Ausbeute 73.0%

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

Ausbeute 73.0%

Lösungsmittel

AcOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with EtOAc (3×200 ml)
2. 2
   WaschenThe combined organic layers were washed with water and brine
3. 3
   Sonstigedried
4. 4
   Sonstigeevaporated in vacuo
5. 5
   Sonstigeto give a pale yellow solid
6. 6
   Sonstigethe solid collected
7. 7
   Waschenwashed with EtOAc
8. 8
   Sonstigedried

Vorschrift

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).

Quelle