Indole → 1-(6-Chlorohexyl)-1H-indole

HRID 1832224Notes

Reaction equation

HRID 1832224 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][Cl:19]>CN(C=O)C.CCOC(C)=O>[Cl:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

6

Reactant 3

HCID 798IndoleHCID 24758Sodium hydrideHCID 805161-Bromo-6-chlorohexane

Product 1

HCID 123407591-(6-Chlorohexyl)-1H-indoleYield 76.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of NaH (0.249 g, 10.0 mmol) in DMF (5 mL) at 0° C. was added a solution of 1-H-indole (0.585 g, 5.00 mmol) in DMF (2 mL). The reaction mixture was stirred for 30 minutes and warmed up to room temperature. Then 1-bromo-6-chlorohexane (0.998 g, 5.00 mmol) was added dropwise by syringe and the reaction mixture was stirred overnight. The reaction mixture was diluted with EtOAc (30 mL), washed with water (3×10 mL), dried over MgSO4, concentrated in vacuo and purified by chromatography using hexane/EtOAc (97.5:2.5) to give the desired product (0.900 g, 76%).

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. washwashed with water (3×10 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography

Sources & evidence

ORD record
ord-4c8ebfb9328544da8f66a6eccec1e444
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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