Piperidine → (E)-1-(4-Hydroxy-3,5-dimethoxyphenyl)-3-(indol-3-yl)-2-propen-1-one

HRID 618127

반응식

HRID 618127 반응식
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10](=[O:12])[CH3:11])=[CH:4][C:3]=1[O:13][CH3:14].[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH:24]=O)=[CH:16]1.N1CCCCC1>C(O)C>[OH:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]([C:10](=[O:12])/[CH:11]=[CH:24]/[C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[NH:15][CH:16]=2)=[CH:6][C:7]=1[O:8][CH3:9]

참가 물질

5

반응물 3

HCID 8082PiperidineHCID 10256Indole-3-CarboxaldehydeHCID 17198Acetosyringone

생성물 1

HCID 21850208(E)-1-(4-Hydroxy-3,5-dimethoxyphenyl)-3-(indol-3-yl)-2-propen-1-one수율 19.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

4'-Hydroxy-3',5'-dimethoxyacetophenone (1.96 g) and indole-3-carboxaldehyde (1.45 g) were dissolved in ethanol (20 ml), and piperidine (0.85 g) was added thereto, followed by heating under reflux for 32 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from ethyl acetate to give Compound 70 (0.62 g).

후처리

  1. temperatureby heating
  2. temperatureunder reflux for 32 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography
  5. customThe obtained crude crystals
  6. customwere recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-74a841b976bc4f10a9a9ce9d1f52035d
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05952355

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