Reaktion #66190

Reaktionsgleichung

tryptamine hydrochloride

ethyl 3-bromopyruvate

charcoal

→

title compound

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

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturto reflux under nitrogen overnight
3. 3
   workup.ADDITIONTEA was added
4. 4
   Temperaturthe reaction mixture was heated
5. 5
   Temperaturto reflux for another 7.5 hours
6. 6
   TemperaturAfter cooling
7. 7
   Sonstigecharcoal was removed by filtration
8. 8
   Waschenwashed with ethanol
9. 9
   EinengenThe filtrate was concentrated under vacuum
10. 10
    workup.ADDITIONdiluted with water (20 mL)
11. 11
    ExtraktionIt was then extracted by EtOAc (3×30 mL)
12. 12
    Waschenthe combined organic layers were washed with brine
13. 13
    Trocknendried over MgSO4
14. 14
    SonstigeEvaporation of solvent and recrystallization from DCM-Hexane

Vorschrift

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+).

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