4-(2-Fluoro-5-methoxybenzyl)pyridine → 4-[(2-Fluoro-5-methoxyphenyl)methyl]piperidine

HRID 273736Notes

Reaction equation

HRID 273736 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1>C(O)(=O)C.[Pt]=O>[F:1][C:2]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:3]=1[CH2:4][CH:5]1[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 158395244-(2-Fluoro-5-methoxybenzyl)pyridine

Product 1

HCID 158395224-[(2-Fluoro-5-methoxyphenyl)methyl]piperidineYield 75.9%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 4-(2-fluoro-5-methoxybenzyl)pyridine (7.7 g, 35.5 mmole) and platinum oxide (0.7 g) in acetic acid (75 ml) was hydrogenated for 3 hr. The catalyst was removed and the acetic acid removed 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 the product (6 g, 75.9%).

Workup

  1. customThe catalyst was removed
  2. customthe acetic acid removed 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-749a33898f224dd68bde9e902e48c11a
Source dataset
uspto-grants-1995_02
Patent number
US05387593

Reaction notes

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