1-Benzyl-3,5-dimethylpiperidin-4-ol → 3,5-Dimethylpiperidin-4-ol

HRID 396308Notes

Reaction equation

HRID 396308 reaction equation
C([N:8]1[CH2:13][CH:12]([CH3:14])[CH:11]([OH:15])[CH:10]([CH3:16])[CH2:9]1)C1C=CC=CC=1>CO.[H][H].[OH-].[Pd+2].[OH-]>[CH3:16][CH:10]1[CH:11]([OH:15])[CH:12]([CH3:14])[CH2:13][NH:8][CH2:9]1

Participants

5

Reactant 1

HCID 230036661-Benzyl-3,5-dimethylpiperidin-4-ol

Product 1

HCID 219737783,5-Dimethylpiperidin-4-ol

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of 1-benzyl-3,5-dimethyl-4-hydroxypiperidine (1.0 g, 4.56 mmole) and 20% palladium hydroxide (0.3 g) in methanol (20 ml) was stirred at room temperature in hydrogen atmosphere (1 atm.) for 4 hr. Catalyst was filtered off, washed with methanol, filtrate was concentrated to dryness to give 3,5-dimethyl-4-hydroxypiperidine. Yield 0.5 g (90%), C7H15NO, m/z 130 (M+1), PMR (CDCl3): 0.9 (6H, m, 2×CH3), 1.44 (1H, m, H3), 1.7 (1H, m, H5), 2.3 (1H, m, H6), 2.46-2.84 (2H, m, H2 & H6), 2.98 (1H, m, H2), 3.3-3.7 (1H, m, H4).

Workup

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

Sources & evidence

ORD record
ord-1471f9fc036741f2b55e7be03f1fa999
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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