3-(1-Acetyl-1,4-dihydro-4-pyridyl)-5-methoxyindole → 5-Methoxy-3-(piperidin-4-yl)-1H-indole

HRID 1252054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1252054
C([N:4]1[CH:9]=[CH:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=3)[NH:12][CH:11]=2)[CH:6]=[CH:5]1)(=O)C.C(N1CCC(C2C3C(=CC=C(OC)C=3)NC=2)CC1)(=O)C>C(O)C.O=[Pt]=O.[OH-].[Na+]>[CH3:20][O:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH:7]1[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]1

Komponenten

6

Edukt 2

HCID 149317413-(1-Acetyl-1,4-dihydro-4-pyridyl)-5-methoxyindoleHCID 201409353-(1-Acetyl-4-piperidyl)-5-methoxyindole

Produkt 1

HCID 432245-Methoxy-3-(piperidin-4-yl)-1H-indoleAusbeute 74,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 345198Adams' catalystKatalysatorHCID 702EthanolLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

3-(1-Acetyl-1,4-dihydro-4-pyridyl)-5-methoxyindole (3.0 g) was dissolved in hot ethanol (150 ml) and hydrogenation was carried out with Adams catalyst (0.25 g). The mixture was filtered and the filtrate was concentrated under reduced pressure to give a residue containing 3-(1-acetyl-4-piperidyl)-5-methoxyindole. This residue was diluted with 2N aqueous sodium hydroxide solution (22 ml) and ethanol (30 ml) and refluxed for 18 hours. Ethanol was then distilled off and the residue was cooled. The precipitate was collected by filtration and recrystallized from a mixture of ethanol and water to give 5-methoxy-3-(4piperidyl)indole (1.92 g).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a residue
  4. temperaturerefluxed for 18 hours
  5. distillationEthanol was then distilled off
  6. temperaturethe residue was cooled
  7. filtrationThe precipitate was collected by filtration
  8. customrecrystallized from a mixture of ethanol and water

Quellen und Nachweise

ORD-Eintrag
ord-78cb878c446b42b484b0c8d4d514b6cc
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04742057

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