Toluene → 4-(2-di-N-propylaminoethyl)indole

HRID 1766626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766626
[NH2:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.I[CH2:14][CH2:15][CH3:16].C([O-])(O)=O.[Na+].[C:22]1(C)[CH:27]=CC=C[CH:23]=1>O>[CH2:14]([N:1]([CH2:23][CH2:22][CH3:27])[CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)[CH2:15][CH3:16]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 336431-Iodopropane2×HCID 516892Sodium Bicarbonate2×HCID 131009012-(1H-Indol-4-yl)ethan-1-amine

Produkt 1

HCID 30860544-(2-di-N-propylaminoethyl)indoleAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4-[(2-amino)ethyl]indole (III) (2.0 g, 12.48 mmol), 1-iodopropane (8.5 g, 50 mmol), NaHCO3 (2.3 g, 27.4 mmol) in toluene (40 mL) was stirred at reflux temperature for 21 h. NaHCO3 (1.15 g, 13.7 mmol) in water (20 mL) and 1-iodopropane (2.12 g, 12.47 mmol) were added to the resultant mixture and was stirred at the same temperature for 6 h. When the mixture reached room temperature, it was filtered and layers were separated. The organic layer was washed with water (15 mL), dried, filtered and evaporated to obtain 2.53 g (83%) of 4-[2-(dipropylamino)ethyl]indole (IV).

Aufarbeitung

  1. temperatureat reflux temperature for 21 h
  2. stirringwas stirred at the same temperature for 6 h
  3. customreached room temperature
  4. filtrationit was filtered
  5. customlayers were separated
  6. washThe organic layer was washed with water (15 mL)
  7. customdried
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-74080961ae8f40ee908b1f1313eed8b7
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07230118B2

Notizen zur Reaktion

Wird geladen…