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

HRID 618127

Reaktionsgleichung

Reaktionsgleichung von HRID 618127
[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]

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 10256Indole-3-CarboxaldehydeHCID 17198Acetosyringone

Produkt 1

HCID 21850208(E)-1-(4-Hydroxy-3,5-dimethoxyphenyl)-3-(indol-3-yl)-2-propen-1-oneAusbeute 19,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-74a841b976bc4f10a9a9ce9d1f52035d
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952355

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