HCID 23003650, compound → HCID 23003701, compound

HRID 396315Notes

Reaction equation

HRID 396315 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([CH2:15][CH2:16][CH3:17])[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[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 1

HCID 23003650HCID 23003650, compound

Product 1

HCID 23003701HCID 23003701, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of 1-benzyl-4-hydroxy-3-n-propylpiperidine (3.3 g, 14.16 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-n-propylpiperidine as oil. Yield 1.8 g (90%), C8H17NO, m/z 144 (M+1), PMR (CDCl3): 0.92 (3H, t, CH3, j=8 Hz), 1.2-1.52 (5H, m, 2×CH2 & H3), 1.72 (1H, m, H5), 1.94 (2H, m, H5, & OH, D2O exchangeable), 2.22 (1H, m, H2), 2.62 (1H, m, H6), 3.12 (1H, m, H2), 3.3 (1H, m, H6), 3.5 (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-3f415a332c9f428ebe6276525e6aee7c
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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