1-Benzyl-4-hydroxy-3-isopropylpiperidine → 4-Hydroxy-3-isopropylpiperidine

HRID 396319Notes

Reaction equation

HRID 396319 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([CH:15]([CH3:17])[CH3:16])[CH2:9]1)C1C=CC=CC=1>CO.[H][H].[OH-].[Pd+2].[OH-]>[OH:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]1[CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 1

HCID 230037111-Benzyl-4-hydroxy-3-isopropylpiperidine

Product 1

HCID 230036734-Hydroxy-3-isopropylpiperidine

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of 1-benzyl-4-hydroxy-3-isopropylpiperidine (2.9 g, 12.44 mmole) and 20% palladium hydroxide (0.25 g) in methanol (25 ml) was stirred in hydrogen atmosphere (1 atm.) for 24 hr at 30° C. Catalyst was filtered off, washed with methanol, filtrate was concentrated to dryness to give 4-hydroxy-3-isopropylpiperidine as oil. Yield 1.6 g (80%), C8H17NO, m/z 144 (M+1) PMR (CDCl3): 0.9 (6H, m, 2×CH3), 1.1-1.64 (2H, m, CH & H3), 1.66-2.42 (3H, m, H5, & OH, D2O exchangeable), 2.62 (1H, m, H2), 3.02 (2H, m, H6), 3.45 (1H, bs, NH, D2O exchangeable), 3.54 (1H, m, H6), 4.18 (1H, m, H4).

Workup

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

Sources & evidence

ORD record
ord-d71304b05bb34ec88cf5bcdf5425136a
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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