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

HRID 275745노트

반응식

HRID 275745 반응식
[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

참가 물질

7

반응물 4

HCID 241BenzeneHCID 798IndoleHCID 80061-Bromo-3-chloropropane2회HCID 24758Sodium hydride

생성물 1

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

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-468dc21213c642339d76bae61e60d4ae
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06352999B1

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