Ethyl Acrylate → HCID 21700152, compound

HRID 1597426Notes

Reaction equation

HRID 1597426 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[CH2:12]>C1COCC1>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:12][CH2:11][C:10]([O:14][CH2:15][CH3:16])=[O:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8821Ethyl Acrylate2×HCID 837951-Acetylpiperazine

Product 1

HCID 21700152HCID 21700152, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-acetylpiperazine (5 g, 39 mmol) in THF (100 mL) was treated with ethyl acrylate (4.2 mL, 39 mmol) then stirred overnight at r.t. after which an additional 4.2 mL of ethyl acrylate was added. The reaction heated at reflux for 5 h, cooled to r.t. and partitioned between dichloromethane and 1N HCl. The acid wash was basified with NaHCO3 to pH 9-10 and extracted 3 times with dichloromethane. Combined organics were dried, filtered and concentrated to give 4.49 g of the title compound as a yellow oil.

Workup

  1. additionwas added
  2. temperatureThe reaction heated
  3. temperatureat reflux for 5 h
  4. custompartitioned between dichloromethane and 1N HCl
  5. washThe acid wash
  6. extractionextracted 3 times with dichloromethane
  7. customCombined organics were dried
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1ed2ae7291a84f33b4ea11911d7a6eac
Source dataset
uspto-grants-2001_09
Patent number
US06294573B1

Reaction notes

Loading…