Indole → 1-Hexyl-1H-indole

HRID 2406632Notes

Reaction equation

HRID 2406632 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[Cl-].[NH4+]>CS(C)=O.C(OCC)(=O)C>[CH2:13]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 798IndoleHCID 81011-BromohexaneHCID 14797Potassium HydroxideHCID 25517Ammonium Chloride

Product 1

HCID 127154041-Hexyl-1H-indole

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1H-indole in DMSO was added KOH at RT and was stirred for 30 minutes. Then to this mixture, 1-bromo-hexane was added and stirred for 3 hours. The reaction was treated with saturated ammonium chloride and ethyl acetate. The product was purified by column chromatography.

Workup

  1. stirringstirred for 3 hours
  2. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-e2f4ee4111df4e23822596d001102ed1
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Reaction notes

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