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

HRID 396303Notes

Reaction equation

HRID 396303 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[C:10]([CH3:16])([CH3:15])[CH2:9]1)C1C=CC=CC=1>CO.[H][H].[OH-].[Pd+2].[OH-]>[CH3:15][C:10]1([CH3:16])[CH:11]([OH:14])[CH2:12][CH2:13][NH:8][CH2:9]1

Participants

5

Reactant 1

HCID 224957201-Benzyl-3,3-dimethylpiperidin-4-OL

Product 1

HCID 219737363,3-Dimethylpiperidin-4-ol

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of 1-benzyl-3,3-dimethyl-4-hydroxypiperidine (5.0 g, 22.0 mmole) and 20% palladium hydroxide (1.5 g) in methanol (100 ml) was stirred at 50-55° C. in hydrogen atmosphere (1 atm.) for 20 hr. Catalyst was filtered off, washed with methanol, filtrate was concentrated to dryness to give 3,3-dimethyl-4-hydroxypiperidine as oil. Yield 2.9 g (94%), C7H15NO, m/z 130 (M+1), PMR (CDCl3): 0.83 (3H, s, CH3), 1.13 (3H, s, CH3), 1.29 (1H, m, H5), 1.45-1.9 (2H, m, H5& H6), 2.4 (1H, d, H2, j=12 Hz), 2.68 (1H, d, H2, j=12 Hz), 3.08 (1H, m, H6), 3.4 (1H, dd, H4, j=6 Hz & 12 Hz).

Workup

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

Sources & evidence

ORD record
ord-c9f618dd8e6f40c3a0823be9696a02fc
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

Loading…