Hydrochloric Acid → N-Ethyl-2-(4-piperidin-4-yl-phenyl)-propionamide

HRID 409721Notes

Reaction equation

HRID 409721 reaction equation
Cl.[CH2:2]([NH:4][C:5](=[O:20])[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[CH3:7])[CH3:3]>C(O)C.[Pt](=O)=O>[CH2:2]([NH:4][C:5](=[O:20])[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)[CH3:7])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86686108N-Ethyl-2-(4-pyridin-4-yl-phenyl)-propionamide

Product 1

HCID 86686109N-Ethyl-2-(4-piperidin-4-yl-phenyl)-propionamide

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

4.4 mL 1N HCl are added to 1.12 g (4.40 mmol) N-ethyl-2-(4-pyridin-4-yl-phenyl)-propionamide (V.1) in 15 mL ethanol. The mixture is hydrogenated (5 bar) for 6 h at rt using 110 mg platinum(IV) oxide. After that time, the catalyst is filtered off and the solvent is evaporated. The residue is taken up in water, alkalized with 1N NaOH and extracted with DCM (2×). The organic layer is dried over magnesium sulphate and the solvent is evaporated. The residue is purified by HPLC (column: Gemini; eluent A: water+0.1% NH4OH, eluent B: MeOH) to yield the desired product.

Workup

  1. customfor 6 h
  2. customat rt
  3. filtrationAfter that time, the catalyst is filtered off
  4. customthe solvent is evaporated
  5. extractionextracted with DCM (2×)
  6. dry with materialThe organic layer is dried over magnesium sulphate
  7. customthe solvent is evaporated
  8. customThe residue is purified by HPLC (column: Gemini; eluent A: water+0.1% NH4OH, eluent B: MeOH)

Sources & evidence

ORD record
ord-75431944cc5e4845872847b2cdb3c85f
Source dataset
uspto-grants-2014_06
Patent number
US08759528B2

Reaction notes

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