5-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester → Allyl-[4-(2,3-dihydro-1H-indol-5-yloxy)-butyl]-methyl-amine

HRID 49500노트

반응식

HRID 49500 반응식
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:24][CH:25]=[CH2:26])[CH3:23])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(Cl)Cl>[CH2:24]([N:22]([CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:8][CH2:9][CH2:10]2)[CH3:23])[CH:25]=[CH2:26]

참가 물질

3

반응물 1

HCID 695147375-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

생성물 1

HCID 21966572Allyl-[4-(2,3-dihydro-1H-indol-5-yloxy)-butyl]-methyl-amine수율 98.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 7.3 g (20.2 mmol) 5-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester in 15 ml CH2Cl2 10 ml trifluoroacetic acid were added at 0° C. The mixture was stirred at reflux for 3 h and was concentrated in vacuo. Water and 2M NaOH were added and the inorganic phase was extracted with ether. The combined organic phases were washed with water and dried over Na2SO4. Evaporation yielded 5.2 g (98%) Allyl-[4-(2,3-dihydro-1H-indol-5-yloxy)-butyl]-methyl-amine as orange oil, MS: 261 (MH+).

후처리

  1. temperatureat reflux for 3 h
  2. concentrationwas concentrated in vacuo
  3. additionWater and 2M NaOH were added
  4. extractionthe inorganic phase was extracted with ether
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over Na2SO4
  7. customEvaporation

출처 및 근거

ORD 기록
ord-55c4c8397a8d4cf08f21aad8eef24a88
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706751B2

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