1-Benzyl-4-hydroxy-4-(6-methoxynaphth-2-yl)piperidine → 4-Hydroxy-4-(6-methoxynaphth-2-yl)-piperidine

HRID 380545Notes

Reaction equation

HRID 380545 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([OH:26])([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH3:25])[CH:20]=3)[CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>[Pd].CO>[OH:26][C:11]1([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH3:25])[CH:20]=3)[CH:15]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 183652491-Benzyl-4-hydroxy-4-(6-methoxynaphth-2-yl)piperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 183652414-Hydroxy-4-(6-methoxynaphth-2-yl)-piperidineYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1.0 gm (2.9 mMol) 1-benzyl-4-hydroxy-4-(6-methoxynaphth-2-yl)piperidine and 5% palladium on carbon in 20 mL methanol was stirred at room temperature under about 1 atmosphere of hydrogen for 6 hours. The reaction mixture was filtered through a bed of CELITE and the filtrate was concentrated under reduced pressure to provide 0.64 gm (86%) of the desired compound as a white foam. A portion of the material was converted to the oxalate salt for analysis.

Workup

  1. filtrationThe reaction mixture was filtered through a bed of CELITE
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2e31b536f79245f2b56f295a7b2b46bf
Source dataset
uspto-grants-2001_10
Patent number
US06303627B1

Reaction notes

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