Water → 7-(3-chloropropoxy)-1H-indole

HRID 2211510Notes

Reaction equation

HRID 2211510 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 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium hydride (0.8 g, 0.017 mol of a 50% oil dispersion) in dimethylformamide (20 ml), under nitrogen, was added dropwise 7-hydroxyindole (2.1 g, 0.0157 mol) in dmethylformamide (20 ml). After complete addition, the reaction was stirred at ambient temperature for 0.5 hor and then cooled to 15° C. To this cooled solution was added, dropwise, 1-bromo-3-chloropropane. (2.5 g, 0.0157 mol) 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 concentratedf to afford a dark brown oil. Following flash chormatography on silica gel 7-(3-chloropropoxy)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. customto afford a dark brown oil
  9. customwas obtained as a colorless oil, 1.0 g

Sources & evidence

ORD record
ord-e7d5586977274598a8a27b77ce978a4b
Source dataset
uspto-grants-2006_09
Patent number
USRE039265E1

Reaction notes

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