Piperazine → 3-Phenyl-1-(piperazin-1-yl)prop-2-en-1-one

HRID 1414197Notes

Reaction equation

HRID 1414197 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:7](Cl)(=[O:16])[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)(Cl)Cl>[C:7]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)(=[O:16])[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 2809493-Phenyl-1-(piperazin-1-yl)prop-2-en-1-oneYield 30%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Absolute piperazine (206 g) was dissolved in 500 ml of chloroform and 66.3 g of cinnamoyl chloride was added gradually at 0° C while mixing. The addition required 3 hours. After mixing was continued for another 2 hr., precipitates were filtered and then the filtrate (chloroform layer) was washed with 50 ml of 5% sodium hydroxide and 50 ml of water. The residues obtained after solvents were distilled away in vacuo were subjected to silica gel column chromatography (eluants were mixtures of chloroform and methanol). Thus crystalline N-cinnamoyl piperazine was obtained. Melting point of the product was 30°-40° C and the product was very hygroscopic. The yield was 30%.

Workup

  1. additionwhile mixing
  2. additionThe addition required 3 hours
  3. additionAfter mixing
  4. custom, precipitates
  5. filtrationwere filtered
  6. washthe filtrate (chloroform layer) was washed with 50 ml of 5% sodium hydroxide and 50 ml of water
  7. customThe residues obtained after solvents
  8. distillationwere distilled away in vacuo

Sources & evidence

ORD record
ord-b6c22d5eb320463f9d9e4c1813b1aa2f
Source dataset
uspto-grants-1977_01
Patent number
US04001223

Reaction notes

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