Ethyl chloroformate → 4-Ethoxycarbonyl-1-(2-pyrrolidone-5-carbonyl)piperazine

HRID 1029399Notes

Reaction equation

HRID 1029399 reaction equation
[NH:1]1[CH:5]([C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])[CH2:4][CH2:3][C:2]1=[O:14].C(=O)([O-])[O-].[K+].[K+].[C:21](Cl)(=[O:25])[O:22][CH2:23][CH3:24]>C(#N)C>[CH2:23]([O:22][C:21]([N:11]1[CH2:10][CH2:9][N:8]([C:6]([CH:5]2[NH:1][C:2](=[O:14])[CH2:3][CH2:4]2)=[O:7])[CH2:13][CH2:12]1)=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 140536931-(2-Pyrrolidone-5-carbonyl)piperazine

Product 1

HCID 140536964-Ethoxycarbonyl-1-(2-pyrrolidone-5-carbonyl)piperazineYield 84.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A mixed solution of 2.1 g of 1-(2-pyrrolidone-5-carbonyl)piperazine, 2.5 g of anhydrous potassium carbonate and 120 ml of acetonitrile was cooled with ice water and 1.1 g of ethyl chlorocarbonate in 10 ml of acetonitrile was dropped therein with stirring. After dropping, the mixture was stirred overnight at room temperature. The solvent was evaporated from the reaction mixture in vacuo, methylene chloride was added to the residue, and insoluble matter was removed therefrom by filtration. The solvent was evaporated in vacuo from the filtrate to give 2.3 g of oily product. This was crystallized from ethyl acetate and further recrystallized to give 2.1 g of desired product, m.p. 147°-148.5° C.

Workup

  1. additionwas dropped
  2. stirringthe mixture was stirred overnight at room temperature
  3. customThe solvent was evaporated from the reaction mixture in vacuo, methylene chloride
  4. additionwas added to the residue, and insoluble matter
  5. customwas removed
  6. filtrationby filtration
  7. customThe solvent was evaporated in vacuo from the filtrate

Sources & evidence

ORD record
ord-c837943f505245a6abfc60d17b48dbb2
Source dataset
uspto-grants-1992_04
Patent number
US05102882

Reaction notes

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