4-(2,5-Difiuorobenzyl)pyridine → 4-[(2,5-Difluorophenyl)methyl]piperidine

HRID 2260500Notes

Reaction equation

HRID 2260500 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:12]([F:15])=[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]([F:15])=[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 200942684-(2,5-Difiuorobenzyl)pyridine

Product 1

HCID 233550784-[(2,5-Difluorophenyl)methyl]piperidineYield 72.9%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of platinum oxide (0.5 g) and 4-(2,5-difiuorobenzyl)pyridine from above in acetic acid (100 ml) was hydrogenated for 3 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 and the extracts concentrated in vacuo. The crude oil was vacuum distilled to give the product (5.1 g, 72.9%, bp: 110° C.). A sample of the hydrochloride was prepared in ether (mp: 182°-183° 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. concentrationthe extracts concentrated in vacuo
  6. distillationdistilled

Sources & evidence

ORD record
ord-e50e7a1a52e84bcb83110f0642f86c1e
Source dataset
uspto-grants-1995_12
Patent number
US05478828

Reaction notes

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