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

HRID 2260498Notes

Reaction equation

HRID 2260498 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 87.6%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 4-(3-methoxybenzyl)pyridine (25 g, 126 mmole) 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, 87.6%). 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-8d47b83719b44f82a5a54f9d2c667199
Source dataset
uspto-grants-1995_12
Patent number
US05478828

Reaction notes

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