HCID 23003686, compound → 3-Ethyl-4-hydroxy-3-methylpiperidine

HRID 396313Notes

Reaction equation

HRID 396313 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[C:10]([CH2:16][CH3:17])([CH3:15])[CH2:9]1)C1C=CC=CC=1>CO.[H][H].[OH-].[Pd+2].[OH-]>[CH2:16]([C:10]1([CH3:15])[CH:11]([OH:14])[CH2:12][CH2:13][NH:8][CH2:9]1)[CH3:17]

Participants

5

Reactant 1

HCID 23003686HCID 23003686, compound

Product 1

HCID 230037053-Ethyl-4-hydroxy-3-methylpiperidine

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of 1-benzyl-3-ethyl-4-hydroxy-3-methylpiperidine (1.1 g, 4.74 mmole) and 20% palladium hydroxide (0.4 g) in methanol (20 ml) was stirred at ambient temperature in hydrogen atmosphere (1 atm.) for 20 hr. Catalyst was filtered off, washed with methanol, filtrate was concentrated to dryness to give 3-ethyl-4-hydroxy-3-methylpiperidine as oil. Yield 0.6 g (90%), C8H17NO, m/z 144 (M+1), PMR (CDCl3): 0.7-1.06 (6H, m, 2×CH3), 1.24-2.0 (5H, m, CH2, H5, NH & OH, NH & OH D2O exchangeable), 2.3 (1H, m, H5), 2.62-3.18 (2H, m, H2), 3.3-3.8 (3H, m, H4 & H6).

Workup

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

Sources & evidence

ORD record
ord-87c86658eece415095692f2d42104be7
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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