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

HRID 273734Notes

Reaction equation

HRID 273734 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-difluorobenzyl)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.). Calc'd. for C12H15F2N.HCl: C, 58.19%; H, 6.52%; N, 5.66%. Found: C, 58.14%; H, 6.56%; N, 5.59%.

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-3e59270ad6cb427cbe872ae0bed39c5c
Source dataset
uspto-grants-1995_02
Patent number
US05387593

Reaction notes

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