Pyridine, 4-[(3-methoxyphenyl)methyl]- → 4-[(3-Methoxyphenyl)methyl]piperidine

HRID 260711Notes

Reaction equation

HRID 260711 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1>C(O)(=O)C.[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1

Participants

4

Reactant 1

HCID 607965Pyridine, 4-[(3-methoxyphenyl)methyl]-

Product 1

HCID 170394894-[(3-Methoxyphenyl)methyl]piperidineYield 88%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 4-(3-methoxybenzyl)pyridine (25 g, 126 mmol) and platinum oxide (2.4 g) in acetic acid (250 ml) was hydrogenated for 2 hr. The catalyst was removed and the solution concentrated in vacuo. The residue was dissolved in water and the solution basified with sodium hydroxide. The basic mixture was extracted with ether. The extracts were dried and concentrated in vacuo. The residue was vacuum distilled to give 4-(3-methoxy-benzyl)piperidine as an oil (22.6 g, 88%). A sample of the hydrochloride was prepared in ether (mp: 146°-147° C.).

Workup

  1. customThe catalyst was removed
  2. concentrationthe solution concentrated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionThe basic mixture was extracted with ether
  5. customThe extracts were dried
  6. concentrationconcentrated in vacuo
  7. distillationdistilled

Sources & evidence

ORD record
ord-9a668d1f794342a2b46a677892227b1b
Source dataset
uspto-grants-1996_06
Patent number
US05530012

Reaction notes

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