4-(4-Ethoxyphenyl)pyridine → 4-(4-Ethoxyphenyl)piperidine

HRID 409734

Reaction equation

HRID 409734 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)[CH3:2]>C(O)(=O)C.[Pt](=O)=O>[CH2:9]1[CH2:4][O:3][CH2:7][CH2:8]1.[CH3:1][OH:3].[NH4+:13].[OH-:3].[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 1

HCID 707009334-(4-Ethoxyphenyl)pyridine

Product 2

HCID 214951914-(4-Ethoxyphenyl)piperidineHCID 86686122THF MeOH NH4OH

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

410 mg (2.06 mmol) 4-(4-Ethoxy-phenyl)-pyridine in 10 mL acetic acid are hydrogenated (3 bar) for 9 h at rt using 50 mg platinum(IV) oxide. After that time, the catalyst is filtered off and the solvent is evaporated. The residue is taken up in 1N NaOH and extracted with EtOAc. The organic layer is dried over sodium sulphate and the solvent is evaporated. The residue is purified by column chromatography (silica gel; DCM:MeOH 9:1, then THF:MeOH:NH4OH 1:1:0.1) to yield the desired product.

Workup

  1. customfor 9 h
  2. customat rt
  3. filtrationAfter that time, the catalyst is filtered off
  4. customthe solvent is evaporated
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer is dried over sodium sulphate
  7. customthe solvent is evaporated
  8. customThe residue is purified by column chromatography (silica gel

Sources & evidence

ORD record
ord-db7752a720184053b3748059490b60bf
Source dataset
uspto-grants-2014_06
Patent number
US08759528B2

Linked notes

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