Piperidine → 5-((E)-(indolin-3-ylidene)methyl)furan-2-carbaldehyde

HRID 555659노트

반응식

HRID 555659 반응식
C([C:3]1[CH:7]=[CH:6][O:5][C:4]=1[CH:8]=[O:9])=O.[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][C:11]1=O.N1CCCC[CH2:21]1>C(O)C>[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)/[C:12](=[CH:21]\[C:6]2[O:5][C:4]([CH:8]=[O:9])=[CH:3][CH:7]=2)/[CH2:11]1

참가 물질

5

반응물 3

HCID 8082PiperidineHCID 321710OxindoleHCID 13814199Furan-2,3-dicarbaldehyde

생성물 1

HCID 866402795-((E)-(indolin-3-ylidene)methyl)furan-2-carbaldehyde수율 31%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

Diformylfuran (1 equivalent) was dissolved in ethanol, and a solution obtained by dissolving oxindole (0.5 equivalent) and piperidine (0.1 equivalent) in ethanol was gradually added thereto. After completion of the addition, the resulting mixture was stirred at room temperature for 2 hours. After completion of the reaction, the resulting precipitate was removed by filtration. To the filtrate, acetone was added and the resulting solution was acidified with a 1 N hydrochloric acid solution and evaporated to dryness under reduced pressure, whereby 5-((E)-(indolin-3-ylidene)methyl)furan-2-carbaldehyde was obtained (yield: 31%). Subsequently, the thus obtained 5-((E)-(indolin-3-ylidene)methyl)furan-2-carbaldehyde (1.2 equivalents), 1-acetyloxindole (1 equivalent) and piperidine (0.1 equivalent) were dissolved in ethanol and the resulting mixture was stirred at room temperature for 12 hours. After completion of the reaction, the resulting precipitate was collected by filtration, washed with cooled ethanol and dried, whereby a target compound was obtained.

후처리

  1. customa solution obtained
  2. additionwas gradually added
  3. additionAfter completion of the addition
  4. customAfter completion of the reaction
  5. customthe resulting precipitate was removed by filtration
  6. additionTo the filtrate, acetone was added
  7. customevaporated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-8f1430175c1540e4a4ec910257ce75e3
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053461B2

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