4-Benzyl-1-methyl-2-oxo-3-phenylpiperazine → 1-Methyl-3-phenylpiperazin-2-one

HRID 1824452Notes

Reaction equation

HRID 1824452 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[C:10](=[O:15])[CH:9]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)C1C=CC=CC=1>C(O)(=O)C.[C].[Pd]>[CH3:14][N:11]1[CH2:12][CH2:13][NH:8][CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]1=[O:15]

Participants

4

Reactant 1

HCID 113465264-Benzyl-1-methyl-2-oxo-3-phenylpiperazine

Product 1

HCID 112869601-Methyl-3-phenylpiperazin-2-oneYield 9.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

4-Benzyl-1-methyl-2-oxo-3-phenylpiperazine (15 g, 0.535 moles) was dissolved in acetic acid (120 ml) and added 5% palladium-carbon (50% wet, 1.5 g). Reaction mass was hydrogenated at 100 psi. After completion of the reaction, reaction mixture was filtered and acetic acid was distilled under reduced pressure. Residue was dissolved in DM water (75 ml). pH was adjusted to 11.0–12.0 with 50% aqueous sodium hydroxide solution. The product was extracted with methylene chloride (2×75 ml) and washed with DM water (75 ml). The methylene chloride layer was concentrated under reduced pressure to obtain 10.1 g of 1-methyl-2-oxo-3-phenylpiperazine.

Workup

  1. customReaction mass
  2. customAfter completion of the reaction, reaction mixture
  3. filtrationwas filtered
  4. distillationacetic acid was distilled under reduced pressure
  5. dissolutionResidue was dissolved in DM water (75 ml)
  6. extractionThe product was extracted with methylene chloride (2×75 ml)
  7. washwashed with DM water (75 ml)
  8. concentrationThe methylene chloride layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-65674cb9c021441484dd334b4a9f123e
Source dataset
uspto-grants-2006_05
Patent number
US07041826B2

Reaction notes

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