Water → 1-(2-Furoyl)piperazine

HRID 1576328Notes

Reaction equation

HRID 1576328 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.O.[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13](Cl)=[O:14].[OH-].[Na+]>CC(C)=O>[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 14798Sodium HydroxideHCID 682422-Furancarbonyl chloride

Product 1

HCID 5502061-(2-Furoyl)piperazine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 21.5 g. (0.25 mol) of piperazine in a mixture of 960 ml. of acidified water (pH = 4.5) and 1200 ml. of acetone, 32.5 g. (0.25 mol) of furoyl chloride are added dropwise while the pH is maintained at 4.5 by dropwise addition of a sodium hydroxide solution. The mixture is made alkaline, and extracted several times with chloroform. The chloroform is distilled off and the concentrated extract is distilled in vacuo. 18.3 g. of the N-(2-furoyl)piperazine thus obtained in 50 ml. of diethyl ether are added to an equivalent amount of cyanogen bromide in a mixture of 60 ml. of water and 60 ml. of diethyl ether. The mixture is stirred overnight at room temperature and then subjected to continuous extraction with benzene. The extract is dried over sodium sulphate and the solvent is distilled off. According to the NMR and IR spectra the residue consists of 1-cyano-4-(2-furoyl)piperazine, m.p. 63°-65°C.

Workup

  1. extractionextracted several times with chloroform
  2. distillationThe chloroform is distilled off
  3. extractionthe concentrated extract
  4. distillationis distilled in vacuo

Sources & evidence

ORD record
ord-0418f104636748d8bfcdbeaa165d81c1
Source dataset
uspto-grants-1976_09
Patent number
US03980650

Reaction notes

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