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

HRID 275745ノート

反応式

HRID 275745 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 220489601-(3-Chloropropyl)-1H-indole収率 83%

試薬・触媒・溶媒 2

HCID 66133Benzyl triethylammonium chloride触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-468dc21213c642339d76bae61e60d4ae
出典データセット
uspto-grants-2002_03
特許番号
US06352999B1

反応ノート

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