Benzene → 1-(3-Chloropropyl)-1H-indole

HRID 275745Notes

Reaction equation

HRID 275745 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[CH2:11][CH2:12][CH2:13][Cl:14].C1C=CC=CC=1.[H-].[Na+]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[Cl:14][CH2:13][CH2:12][CH2:11][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 241BenzeneHCID 798IndoleHCID 80061-Bromo-3-chloropropane2×HCID 24758Sodium hydride

Product 1

HCID 220489601-(3-Chloropropyl)-1H-indoleYield 83%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

To a stirred mixture of 58.5 g of 1H-indole, 107.5 ml of 1-bromo-3-chloropropane, 15 mg of N,N,N-triethylbenzenemethanaminium chloride and 450 ml of benzene were added dropwise, during a period of 30 minutes, 250 ml of a sodium hydride dispersion 60% at 40° C. Upon completion, stirring was continued for 1 hour at 40° C. Another amount of 15 ml of 1-bromo-3-chloropropane was added and stirring was continued for 1 hour at 50° C. After cooling, the reaction mixture was poured into water. The product was extracted with benzene. The extract was separated, dried, filtered and evaporated. The residue was distilled, yielding 80 ml (83%) of 1-(3-chloropropyl)-1H-indole (interm. 10); bp. 120-125° C.

Workup

  1. additionwere added dropwise, during a period of 30 minutes
  2. customat 40° C
  3. stirringstirring
  4. waitwas continued for 1 hour at 50° C
  5. temperatureAfter cooling
  6. extractionThe product was extracted with benzene
  7. customThe extract was separated
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. distillationThe residue was distilled

Sources & evidence

ORD record
ord-468dc21213c642339d76bae61e60d4ae
Source dataset
uspto-grants-2002_03
Patent number
US06352999B1

Reaction notes

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