Hydrochloric Acid → 2-Phenylpiperidine

HRID 2252654Notes

Reaction equation

HRID 2252654 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[OH-].[Na+]>CCO.[Pt]=O>[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 138872-PhenylpyridineHCID 14798Sodium Hydroxide

Product 1

HCID 1030202-Phenylpiperidine

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

2-Phenylpyridine, Intermediate 14, (4.0 g, 25.81 mmol), and concentrated HCl (3 mL) in EtOH (15 mL) were treated with platinum oxide and subjected to catalytic hydrogenation (˜1 atm, balloon), at room temperature for 72 hours. After removal of the catalyst by filtration, the solution was evaporated in vacuo to a pale yellow HCl salt of the product. The free base is obtained by treating the residue with 10% aqueous sodium hydroxide. The aqueous is then extracted with Et2O several times and the extracts dried (MgSO4) and evaporated to an oil to give the title compound.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe solution was evaporated in vacuo to a pale yellow HCl salt of the product
  4. customThe free base is obtained
  5. extractionThe aqueous is then extracted with Et2O several times
  6. dry with materialthe extracts dried (MgSO4)
  7. customevaporated to an oil

Sources & evidence

ORD record
ord-ab38fd919bbe41b688208f54298c7a37
Source dataset
uspto-grants-2008_01
Patent number
US07323464B2

Reaction notes

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