1-Benzyl-4-hydroxy-4-(naphth-1-yl)piperidine → 4-Hydroxy-4-(1-naphthyl)piperidine

HRID 1416197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1416197
C([N:8]1[CH2:13][CH2:12][C:11]([OH:24])([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>[Pd].CO>[OH:24][C:11]1([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Komponenten

4

Edukt 1

HCID 183653421-Benzyl-4-hydroxy-4-(naphth-1-yl)piperidine

Produkt 1

HCID 151248114-Hydroxy-4-(1-naphthyl)piperidineAusbeute 49,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 1.5 gm (4.7 mMol) 1-benzyl-4-hydroxy-4-(naphth-1-yl)piperidine and 0.1 gm 5% palladium on carbon in 45 mL methanol was stirred under a hydrogen atmosphere for 2 days at room temperature. The reaction mixture was then filtered through a bed of celite and the filtrate concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with dichloromethane containing 17% methanol. Fractions containing product were combined and concentrated under reduced pressure to provide 0.526 gm (49%) of the title compound as a white solid.

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered through a bed of celite
  2. concentrationthe filtrate concentrated under reduced pressure
  3. washeluting with dichloromethane containing 17% methanol
  4. additionFractions containing product
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5827544fda0445af82b153be17811a2b
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05912256

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