反応 #66190

反応方程式

tryptamine hydrochloride

ethyl 3-bromopyruvate

charcoal

→

title compound

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

溶媒

ethanol

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度to reflux under nitrogen overnight
3. 3
   workup.ADDITIONTEA was added
4. 4
   温度the reaction mixture was heated
5. 5
   温度to reflux for another 7.5 hours
6. 6
   温度After cooling
7. 7
   その他charcoal was removed by filtration
8. 8
   洗浄washed with ethanol
9. 9
   濃縮The filtrate was concentrated under vacuum
10. 10
    workup.ADDITIONdiluted with water (20 mL)
11. 11
    抽出It was then extracted by EtOAc (3×30 mL)
12. 12
    洗浄the combined organic layers were washed with brine
13. 13
    乾燥dried over MgSO4
14. 14
    その他Evaporation of solvent and recrystallization from DCM-Hexane

実験手順

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+).

出典