Ethyl Acetate → 4-Benzylpiperazine-2,6-dione

HRID 467530

Reaction equation

HRID 467530 reaction equation
[CH2:1]([N:8]([CH2:13][C:14]([OH:16])=O)[CH2:9][C:10](O)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[NH4+:20].C(OCC)(=O)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][C:14](=[O:16])[NH:20][C:10](=[O:11])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 77606N-Benzylaminodiacetic acidHCID 516892Sodium BicarbonateHCID 2723923Ammonium formate

Product 1

HCID 5609674-Benzylpiperazine-2,6-dioneYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

A suspension of 2,2′-(benzylazanediyl)diacetic acid (5.0 g, 22.4 mmol) and ammonium formate (4.2 g, 67.2 mmol) in N,N-dimethylformamide (75 mL) was stirred to reflux (160° C.) for 2 days. After cooling to room temperature, the reaction mixture was diluted by successive addition of ethyl acetate (150 mL) and a saturated solution of sodium hydrogen carbonate (150 mL). The aqueous layer was extracted with ethyl acetate (2×150 mL) and the combined organic phases were washed with a saturated solution of sodium chloride (3×100 mL), dried over sodium sulfate, filtered and concentrated under vacuum to give the title product as a yellow liquid (3.96 g, 87%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×150 mL)
  3. washthe combined organic phases were washed with a saturated solution of sodium chloride (3×100 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-48116873b693424a91ee82b72059115e
Source dataset
uspto-grants-2014_01
Patent number
US08623865B2

Linked notes

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