Piperazine → o-Methoxycarbonyl-alpha-(1-piperazinyl)acetanilide

HRID 1381184Notes

Reaction equation

HRID 1381184 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:8][C:9]([NH:11][C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[C:14]([O:16][CH3:17])=[O:15])=[O:10]>C(O)C>[CH3:17][O:16][C:14]([C:13]1[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=1[NH:11][C:9](=[O:10])[CH2:8][N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)=[O:15]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 295954Methyl 2-[(chloroacetyl)amino]benzoate

Product 1

HCID 13117362o-Methoxycarbonyl-alpha-(1-piperazinyl)acetanilide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.3 Grams of piperazine was added to 50 ml of ethanol, to this solution was added 2.3 g of methyl o-(α-chloroacetylamino)benzoate at a temperature of 40°-50° C. with stirring. The reaction mixture was stirred at the same temperature for 3 hours, then the reaction mixture was concentrated, to the obtained residue was added 20 ml of water, then saturated with sodium chloride, and extracted with chloroform. The chloroform layer was washed with a 10%-sodium hydroxide solution, then washed with a small amount of water and dried. After removal of the solvent by distillation, the residue obtained was purified by a silica gel column chromatography, and recrystallized from ether to obtain 2 g of o-methoxycarbonyl-α-(1-piperazinyl)-acetanilide in the form of colorless needle-like crystals. Melting point: 94°-96° C.

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 3 hours
  2. concentrationthe reaction mixture was concentrated, to the obtained residue
  3. additionwas added 20 ml of water
  4. extractionsaturated with sodium chloride, and extracted with chloroform
  5. washThe chloroform layer was washed with a 10%-sodium hydroxide solution
  6. washwashed with a small amount of water
  7. customdried
  8. customAfter removal of the solvent
  9. distillationby distillation
  10. customthe residue obtained
  11. customwas purified by a silica gel column chromatography
  12. customrecrystallized from ether

Sources & evidence

ORD record
ord-8194e563d1154bfb972dafdb7e017474
Source dataset
uspto-grants-1986_04
Patent number
US04585774

Reaction notes

Loading…