Methyl iodide → 5-Chloro-2-heptyl-1-methyl-1H-indole

HRID 2406675Notes

Reaction equation

HRID 2406675 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5]2.[OH-].[K+].I[CH3:21]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:21])[C:6]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 687502635-chloro-2-heptyl-1H-indole

Product 1

HCID 687494535-Chloro-2-heptyl-1-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To the solution of 5-chloro-2-heptyl-1H-indole in DMSO was added KOH at RT and was stirred for 30 minutes. Then to this mixture, iodomethane was added and stirred for 3 hours. The reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The product, 5-chloro-2-heptyl-1-methyl-1H-indole was purified by column chromatography.

Workup

  1. stirringstirred for 3 hours
  2. customThe reaction was quenched with saturated ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. customThe product, 5-chloro-2-heptyl-1-methyl-1H-indole was purified by column chromatography

Sources & evidence

ORD record
ord-baac91965f8145faa0e5077a0881266a
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Reaction notes

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