Reacción #66190

Ecuación de reacción

tryptamine hydrochloride

ethyl 3-bromopyruvate

charcoal

→

title compound

Ethyl 1,2,3,6-Tetrahydroazepino[4,5-b]Indole-5-Carboxylate

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturato reflux under nitrogen overnight
3. 3
   workup.ADDITIONTEA was added
4. 4
   Temperaturathe reaction mixture was heated
5. 5
   Temperaturato reflux for another 7.5 hours
6. 6
   TemperaturaAfter cooling
7. 7
   Otrocharcoal was removed by filtration
8. 8
   Lavadowashed with ethanol
9. 9
   ConcentraciónThe filtrate was concentrated under vacuum
10. 10
    workup.ADDITIONdiluted with water (20 mL)
11. 11
    ExtracciónIt was then extracted by EtOAc (3×30 mL)
12. 12
    Lavadothe combined organic layers were washed with brine
13. 13
    Secadodried over MgSO4
14. 14
    OtroEvaporation of solvent and recrystallization from DCM-Hexane

Procedimiento

A mixture of tryptamine hydrochloride (1.96 g, 10 mmol), ethyl 3-bromopyruvate (1.67 mL, 1.2 equiv) and decolorizing charcoal (0.5 g) in absolute ethanol was heated to reflux under nitrogen overnight. TEA was added and the reaction mixture was heated to reflux for another 7.5 hours. After cooling, charcoal was removed by filtration and washed with ethanol. The filtrate was concentrated under vacuum and diluted with water (20 mL). It was then extracted by EtOAc (3×30 mL) and the combined organic layers were washed with brine and dried over MgSO4. Evaporation of solvent and recrystallization from DCM-Hexane gave the title compound (1.17 g). 1H-NMR (CDCl3): δ 10.49 (1 H, br s), 7.79 (1H, d), 7.43 (1H, d), 7.43 (1 H, d), 7.06 (2H, m), 5.27 (1H, br s), 4.29 (2H, q) 3.58 (2H, m), 3.17 (2H, m), 1.36 (3H, t); MS (ES): 257 (MH+).

Fuente