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

HRID 1766626Notes

Reaction equation

HRID 1766626 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-74080961ae8f40ee908b1f1313eed8b7
Source dataset
uspto-grants-2007_06
Patent number
US07230118B2

Reaction notes

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