Water → 7-(3-chloropropoxy)-1H-indole

HRID 2184521Notes

Reaction equation

HRID 2184521 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2.Br[CH2:14][CH2:15][CH2:16][Cl:17].O>CN(C)C=O>[Cl:17][CH2:16][CH2:15][CH2:14][O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2

Participants

6

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 27376517-Hydroxyindole

Product 1

HCID 153849647-(3-chloropropoxy)-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred suspension of sodium hydride (0.8 g, 17 mmol of a 50% oil dispersion in dimethylformamide (20 ml), under nitrogen, was added dropwise 7-hydroxyindole (2.1 g, 15.7 mmol) in dimethylformamide (20 ml). After complete addition, the reaction was stirred at ambient temperature for 0.5 hour and then cooled to 15° C. To this cooled solution was added, dropwise, 1-bromo-3-chloropropane (2.5 g, 15.7 mmol) in dimethylformamide (5 ml). The reaction was then stirred at ambient temperature for 16 hours. The reaction was poured into water, and the aqueous suspension extracted with ethyl acetate. The ethyl acetate was washed with water, dried (MgSO4), and the solvent was concentrated to afford a dark brown oil. Following flash chromatography an silica gel. 7-(3-chloropropoxy)indole was obtained as a colorless oil, 1.0 g. ANALYSIS: Calculated for C11H12ClNO: 63.01%C 5.77%H 6.68%,N Found: 63.25%C 5.61%H 6.65%N

Workup

  1. additionAfter complete addition
  2. temperaturecooled to 15° C
  3. additionTo this cooled solution was added
  4. stirringThe reaction was then stirred at ambient temperature for 16 hours
  5. extractionthe aqueous suspension extracted with ethyl acetate
  6. washThe ethyl acetate was washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationthe solvent was concentrated
  9. customto afford a dark brown oil

Sources & evidence

ORD record
ord-5921c3d8e00f422486ce683c020e6413
Source dataset
uspto-grants-2002_06
Patent number
USRE037729E1

Reaction notes

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