1-Benzyl-3,5-dimethyl-3-ethyl-4-hydroxypiperidine → 3,5-Dimethyl-3-ethyl-4-hydroxypiperidine

HRID 396337Notes

Reaction equation

HRID 396337 reaction equation
C([N:8]1[CH2:13][CH:12]([CH3:14])[CH:11]([OH:15])[C:10]([CH3:18])([CH2:16][CH3:17])[CH2:9]1)C1C=CC=CC=1>CO.[H][H].[OH-].[Pd+2].[OH-]>[CH3:18][C:10]1([CH2:16][CH3:17])[CH:11]([OH:15])[CH:12]([CH3:14])[CH2:13][NH:8][CH2:9]1

Participants

5

Reactant 1

HCID 230036911-Benzyl-3,5-dimethyl-3-ethyl-4-hydroxypiperidine

Product 1

HCID 230036803,5-Dimethyl-3-ethyl-4-hydroxypiperidine

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of 1-benzyl-3,5-dimethyl-3-ethyl-4-hydroxypiperidine (2.9 g, 11.74 mmole) and 20% palladium hydroxide (0.5 g) in methanol (20 ml) was stirred in hydrogen atmosphere (1 atm.) for 8 hr at 35° C. Catalyst was filtered off, washed with methanol, filtrate was concentrated to dryness to give 3,5-dimethyl-3-ethyl-4-hydroxypiperidine as oil. Yield 1.7 g (93%), C9H19NO, m/z 158 (M+1).

Workup

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

Sources & evidence

ORD record
ord-ab6dfa7b91e8455d9e544d86e4d60c23
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

Loading…