1-Benzyl-3-ethyl-4-hydroxypiperidine → 3-Ethylpiperidin-4-ol

HRID 396305Notes

Reaction equation

HRID 396305 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([CH2:15][CH3:16])[CH2:9]1)C1C=CC=CC=1>CO.[H][H].[OH-].[Pd+2].[OH-]>[CH2:15]([CH:10]1[CH:11]([OH:14])[CH2:12][CH2:13][NH:8][CH2:9]1)[CH3:16]

Participants

5

Reactant 1

HCID 230037101-Benzyl-3-ethyl-4-hydroxypiperidine

Product 1

HCID 219737483-Ethylpiperidin-4-ol

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalyst2×HCID 887MethanolSolvent2×HCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of 1-benzyl-3-ethyl-4-hydroxypiperidine (5.0 g, 22.0 mmole) and palladium hydroxide (1.5 g) in methanol (100 ml) was stirred at 5.0 g, 22.0 mmole) and palladium hydroxide (1.5 g) in methanol (100 ml) was stirred at 50-55° C. in hydrogen atmosphere (1 atm.) for 20 hr. The catalyst was filtered off, washed with methanol, and filtrate was concentrated to dryness to give 3-ethyl-4-hydroxypiperidine as oil. Yield 2.9 g (94%), C7H15NO, m/z 130 (M+1).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with methanol, and filtrate
  3. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-8eda4e99072d423ca3f7f36185454433
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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