反応 #82489

反応方程式

Bis(2-chloroethyl)amine hydrochloride

5-aminoindole

sodium carbonate

→

1-(5-indolyl)piperazine

収率 18.5%

溶媒

ethanol

反応条件

後処理

1. 1
   温度the mixture heated
2. 2
   温度at reflux for 16 h
3. 3
   温度to cool
4. 4
   温度the reaction mixture heated
5. 5
   温度at reflux for 8 h
6. 6
   温度to cool
7. 7
   ろ過filtered
8. 8
   その他the filtrate evaporated
9. 9
   workup.DISSOLUTIONThe residue was dissolved in 1M hydrochloric acid (100 ml)
10. 10
    抽出extracted with dichloromethane (2×50 ml)
11. 11
    抽出extracted with ethyl acetate (2×100 ml)
12. 12
    洗浄The extracts were washed with brine (100 ml)
13. 13
    乾燥dried (MgSO4)
14. 14
    その他The residue from evaporation of the extracts
15. 15
    その他was purified by flash chromatography
16. 16
    洗浄eluting with dichloromethane/methanol/ammonia

実験手順

Bis(2-chloroethyl)amine hydrochloride (3.60 g, 20.2 mmol) was added to a suspension of 5-aminoindole (2.53 g, 19.1 mmol) in ethanol (30 ml) and the mixture heated at reflux for 16 h. The mixture was allowed to cool, sodium carbonate (2.14 g, 20.2 mmol) was added and the reaction mixture heated at reflux for 8 h. The mixture was allowed to cool, filtered and the filtrate evaporated. The residue was dissolved in 1M hydrochloric acid (100 ml) and extracted with dichloromethane (2×50 ml). The aqueous phase was made basic with 4M sodium hydroxide (30 ml) and extracted with ethyl acetate (2×100 ml). The extracts were washed with brine (100 ml), combined and dried (MgSO4). The residue from evaporation of the extracts was purified by flash chromatography, eluting with dichloromethane/methanol/ammonia, to give 1-(5-indolyl)piperazine (0.71 g, 18%), as a cream solid; δH (DMSO-d6) 2.94 (4H, m, 2×piperazinyl CH2), 3.00 (4H, m, 2×piperazinyl CH2), 6.29 (1H, m, 3-H), 6.84 (1H, dd, J 9.0, 2.0 Hz, 6-H), 7.00 (1H, d, J 2.0 Hz, 2-H), 7.24 (2H, m, 4-H, 7-H), and 10.82 (1H, br s, NH).

出典