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1-Bromo-3-chloropropane → 3-(3-Chloropropyl)-7-methanesulfonyloxy-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 33214
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HRID 33214 반응식
[CH3:1][S:2]([O:5][C:6]1[CH:16]=[CH:15][C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14][C:8]=2[CH:7]=1)(=[O:4])=[O:3].Br[CH2:18][CH2:19][CH2:20][Cl:21].C(N(CC)CC)C>O1CCCC1>[Cl:21][CH2:20][CH2:19][CH2:18][N:12]1[CH2:11][CH2:10][C:9]2[CH:15]=[CH:16][C:6]([O:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:7][C:8]=2[CH2:14][CH2:13]1
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참가 물질

5

반응물 3

HCID 80061-Bromo-3-chloropropaneHCID 8471TriethylamineHCID 112994727-Methanesulfonyloxy-2,3,4,5-tetrahydro-1H-3-benzazepine

생성물 1

HCID 865941693-(3-Chloropropyl)-7-methanesulfonyloxy-2,3,4,5-tetrahydro-1H-3-benzazepine수율 53%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 7-methanesulfonyloxy-2,3,4,5-tetrahydro-1H-3-benzazepine (1.75 g, 7.3 mmol), 1-bromo-3-chloropropane (0.80 ml, 8.1 mmol) and triethylamine (3 ml, 21.5 mmol) in anhydrous tetrahydrofuran (25 ml) was heated at reflux for 5 h. The mixture was cooled, evaporated in vacuo and the residue partitioned between water (100 ml) and ethyl acetate (100 ml). The aqueous layer was extracted with ethyl acetate (100 ml) and the combined organics washed with brine (150 ml), dried (Na2SO4) and evaporated in vacuo. Purification by chromatography on silica gel using 10-70% ethyl acetate in hexane gradient elution gave the title compound as a pale orange oil (1.22 g, 53%).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. temperatureThe mixture was cooled
  4. customevaporated in vacuo
  5. customthe residue partitioned between water (100 ml) and ethyl acetate (100 ml)
  6. extractionThe aqueous layer was extracted with ethyl acetate (100 ml)
  7. washthe combined organics washed with brine (150 ml)
  8. dry with materialdried (Na2SO4)
  9. customevaporated in vacuo
  10. customPurification by chromatography
  11. washon silica gel using 10-70% ethyl acetate in hexane gradient elution

출처 및 근거

ORD 기록
ord-262dcd86f3344f1cb62cd95887629c16
출처 데이터셋
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07429579B2

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