Indole → 1-(3-Chloropropyl)-1H-indole

HRID 50994Notes

Reaction equation

HRID 50994 reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.[OH-].[K+]>CN(C=O)C>[Cl:5][CH2:4][CH2:3][CH2:2][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1

Participants

5

Reactant 3

HCID 798IndoleHCID 80061-Bromo-3-chloropropaneHCID 14797Potassium Hydroxide

Product 1

HCID 220489601-(3-Chloropropyl)-1H-indoleYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 1-bromo-3-chloropropane (2.00 g, 12.7 mmol) in DMF (7.0 mL) was added indole (500 mg, 4.24 mmol) followed by powdered KOH (262 mg, 4.66 mmol) at 20° C. The reaction mixture was then stirred for 15 h at 20° C. The reaction was quenched by addition of H2O and the product was extracted with Et2O. The organic solution was washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. 1-(3-Chloro-1-propyl)indole (580 mg, 71%) was isolated by flash chromatography on a silica gel column by elution with EtOAc/Hexanes a pale yellow oil. 1H NMR (CDCl3, 300 MHz) δ2.28 (qu, 2H, J=6.3 Hz), 3.46 (t, 2H, J=6.2 Hz), 4.36 (t, 2H, J=6.6 Hz), 6.51 (d, 1H, J=3.3 Hz), 7.09-7.18 (m, 2H), 7.20-7.25 (m, 1H), 7.38 (d, 1H, J=8.5 Hz), 7.64 (d, 1H, J=7.7 Hz) ppm.

Workup

  1. customThe reaction was quenched by addition of H2O
  2. extractionthe product was extracted with Et2O
  3. washThe organic solution was washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc1cbfbde0614814af42b2aeb590a66b
Source dataset
uspto-grants-2004_03
Patent number
US06713471B1

Reaction notes

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