Water → 7-(3-chloropropoxy)-1H-indole

HRID 357375

Reaction equation

HRID 357375 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 on silica gel, 7-(3chloropropoxy)indole was obtained as a colorless oil, 1.0 g.

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-bda9d6c8309b46a4a575f631220bd48b
Source dataset
uspto-grants-1998_11
Patent number
US05840727

Linked notes

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