Ethylenediamine → 3-Phenylpiperazin-2-one

HRID 2252651Notes

Reaction equation

HRID 2252651 reaction equation
CO[C:3]([CH:5](Br)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[CH2:13]([NH2:16])[CH2:14][NH2:15].C[O-].[Na+]>CO>[C:6]1([CH:5]2[NH:16][CH2:13][CH2:14][NH:15][C:3]2=[O:4])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 2506813-Phenylpiperazin-2-oneYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl bromophenyl acetate (25 g, 109 mmol) and ethylene diamine (13.1 g, 218 mmol) were mixed in dry MeOH (180 mL) and stirred at room temperature for 15 minutes under nitrogen. Sodium methoxide (6.5 g, 120 mmol) was added in one portion and the mixture heated to reflux for 3.5 hr. The mixture was left stirring overnight at room temperature. The solvent was evaporated in vacuo to give a pale yellow gum, which was partitioned between water (100 mL) and chloroform (100 mL), the pH of the aqueous phase was adjusted with 2M HCl to pH 7.5 and extracted with more chloroform (100 mL). The combined organic phases were dried (MgSO4) and evaporated to give the title compound as a pale yellow solid (17 g, 89%).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 3.5 hr
  3. waitThe mixture was left
  4. stirringstirring overnight at room temperature
  5. customThe solvent was evaporated in vacuo
  6. customto give a pale yellow gum, which
  7. customwas partitioned between water (100 mL) and chloroform (100 mL)
  8. extractionextracted with more chloroform (100 mL)
  9. dry with materialThe combined organic phases were dried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-a4b6b029ff954c4c90141fce5ef34d20
Source dataset
uspto-grants-2008_01
Patent number
US07323464B2

Reaction notes

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