Reaktion #82489

Reaktionsgleichung

Bis(2-chloroethyl)amine hydrochloride

5-aminoindole

sodium carbonate

→

1-(5-indolyl)piperazine

Ausbeute 18.5%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture heated
2. 2
   Temperaturat reflux for 16 h
3. 3
   Temperaturto cool
4. 4
   Temperaturthe reaction mixture heated
5. 5
   Temperaturat reflux for 8 h
6. 6
   Temperaturto cool
7. 7
   Filtrationfiltered
8. 8
   Sonstigethe filtrate evaporated
9. 9
   workup.DISSOLUTIONThe residue was dissolved in 1M hydrochloric acid (100 ml)
10. 10
    Extraktionextracted with dichloromethane (2×50 ml)
11. 11
    Extraktionextracted with ethyl acetate (2×100 ml)
12. 12
    WaschenThe extracts were washed with brine (100 ml)
13. 13
    Trocknendried (MgSO4)
14. 14
    SonstigeThe residue from evaporation of the extracts
15. 15
    Sonstigewas purified by flash chromatography
16. 16
    Wascheneluting with dichloromethane/methanol/ammonia

Vorschrift

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).

Quelle