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

HRID 2260502Notes

Reaction equation

HRID 2260502 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-0bb8a8127d984ccda13d8a111a3103af
Source dataset
uspto-grants-1995_12
Patent number
US05478828

Reaction notes

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