Indole → 1-(3-Bromopropyl)indole

HRID 1027341Notes

Reaction equation

HRID 1027341 reaction equation
[OH-].[K+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[Br:12][CH2:13][CH2:14][CH2:15]Br.CN(C)C=O>O>[Br:12][CH2:13][CH2:14][CH2:15][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 4

HCID 798IndoleHCID 6228DimethylformamideHCID 80011,3-DibromopropaneHCID 14797Potassium Hydroxide

Product 1

HCID 118590271-(3-Bromopropyl)indoleYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

9.58 g of potassium hydroxide (KOH) and 20.00 g of indole were added to 110.58 g of 1,3-dibromopropane and 450 mL of N,N-dimethylformamide (DMF), and the mixture was stirred at 70° C. for 8 hours. After cooling to room temperature, 1 L of distilled water was added to the reaction solution, and the resulting solution was extracted with 1 L of ethyl acetate. The organic layer was washed with 500 mL of distilled water five times, then concentrated and purified by column chromatography to obtain 27.24 g of N-(3-bromopropyl)-indole. Compounds (p-9) and (p-10) having a bromopropyl group shown below were also synthesized in the same manner.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe resulting solution was extracted with 1 L of ethyl acetate
  3. washThe organic layer was washed with 500 mL of distilled water five times
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-932ecd867fc84d1e91ecce733a5d9ae3
Source dataset
uspto-grants-2014_05
Patent number
US08735048B2

Reaction notes

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