Reacción #516367

Ecuación de reacción

4-piperidone hydrochloride hydrate

phosphoric acid

2-Phenylindole

EtOAc

→

title compound

Rendimiento 73.0%

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

Rendimiento 73.0%

Disolventes

AcOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with EtOAc (3×200 ml)
2. 2
   LavadoThe combined organic layers were washed with water and brine
3. 3
   Otrodried
4. 4
   Otroevaporated in vacuo
5. 5
   Otroto give a pale yellow solid
6. 6
   Otrothe solid collected
7. 7
   Lavadowashed with EtOAc
8. 8
   Otrodried

Procedimiento

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).

Fuente