HCID 70028630, compound → HCID 45083227, compound

HRID 396321Notes

Reaction equation

HRID 396321 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:9]1)C1C=CC=CC=1>CO.[H][H].[OH-].[Pd+2].[OH-]>[CH2:15]([CH:10]1[CH:11]([OH:14])[CH2:12][CH2:13][NH:8][CH2:9]1)[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 1

HCID 70028630HCID 70028630, compound

Product 1

HCID 45083227HCID 45083227, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of 1-benzyl-3-n-butyl-4-hydroxypiperidine (2.5 g, 10.0 mmole) and 20% palladium hydroxide (0.2 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 3-n-butyl-4-hydroxypiperidine as oil. Yield 1.4 g (87%), C9H19NO, m/z 158 (M+1) PMR (CDCl3): 0.94 (3H, t, CH3, j=8 Hz), 1.04-1.54 (7H, m, 3×CH2 & H3), 1.74 (1H, m, H5), 1.98 (2H, m, H5, & OH, D2O exchangeable), 2.22 (1H, m, H2), 2.7 (1H, m, H6), 3.12 (1H, m, H2), 3.3 (1H, m, H6), 3.46 (1H, bs, NH, D2O exchangeable), 3.98 (1H, m, H4).

Workup

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

Sources & evidence

ORD record
ord-dd458bf80ad14a809bbb92813067d02e
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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