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Cyclopropylamine → (E)-N-cyclopropyl-2-(6-fluoro-1-indanylidene)acetamide

HRID 362814
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HRID 362814 반응식
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7]/[C:8]/2=[CH:11]\[C:12](Cl)=[O:13])=[CH:4][CH:3]=1.[CH:15]1([NH2:18])[CH2:17][CH2:16]1>ClCCl>[CH:15]1([NH:18][C:12](=[O:13])/[CH:11]=[C:8]2\[CH2:7][CH2:6][C:5]3[C:9]\2=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:17][CH2:16]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 69828CyclopropylamineHCID 15491026(E)-2-(6-fluoro-1-indanylidene)acetyl chloride

생성물 1

HCID 11746481(E)-N-cyclopropyl-2-(6-fluoro-1-indanylidene)acetamide수율 76%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To an ice-cold stirred solution of (E)-2-(6-Fluoro-1-indanylidene)acetyl Chloride in dichloromethane (50 ml) was added cyclopropylamine (1.65 g, 28.86 mmol) and the reaction was warmed to room temperature overnight. The reaction was evaporated in vacuo to a solid residue. This residue was dissolved in ethyl acetate (300 ml), washed with water (75 ml), and the organic layer was concentrated by spin evaporation in vacuo. The residue was chromatographed on silica gel using ethyl acetate-hexanes (0:1 to 1:1 gradient) as eluent. Fractions containing only the product were combined and concentrated by spin evaporation in vacuo. Recrystallization of the residue from dichloromethane-hexanes gave 1.6 g (76%) of (E)-N-cyclopropyl-2-(6-fluoro-1-indanylidene)acetamide as a white powdery solid, m.p. 124°-127° C.;

후처리

  1. customThe reaction was evaporated in vacuo to a solid residue
  2. dissolutionThis residue was dissolved in ethyl acetate (300 ml)
  3. washwashed with water (75 ml)
  4. concentrationthe organic layer was concentrated by spin evaporation in vacuo
  5. customThe residue was chromatographed on silica gel
  6. additionFractions containing only the product
  7. concentrationconcentrated by spin evaporation in vacuo
  8. customRecrystallization of the residue from dichloromethane-hexanes

출처 및 근거

ORD 기록
ord-f28f8da353d742edb4649fbe1be1acae
출처 데이터셋
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05872118

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