Piperazine → HCID 3787305, compound

HRID 2287137Notes

Reaction equation

HRID 2287137 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:7]([O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[CH:8]1[O:10][CH2:9]1>CO>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:7][CH:8]([OH:10])[CH2:9][N:1]2[CH2:6][CH2:5][N:4]([CH2:9][CH:8]([OH:10])[CH2:7][O:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[CH2:3][CH2:2]2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 915152-((4-Chlorophenoxy)methyl)oxirane

Product 1

HCID 3787305HCID 3787305, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

While 9.3 g of piperazine is refluxed in 50 ml of methanol with stirring, 10 g of p-chlorophenyl glycidyl ether are added dropwise over a period of 1.5 hours. After the addition has been completed, the mixture is refluxed with stirring for a further 1.5 hours, and then concentrated to dryness under reduced pressure. The residue is dissolved in dilute hydrochloric acid and extracted with ethyl acetate. The water layer is rendered basic with sodium hydroxide, extracted first with benzene from which there can be obtained N,N'-bis[3-(4-chlorophenoxy)-2-hydroxypropyl]piperazine, and then with n-butanol. The butanol extracts are washed with water and the solvent then removed by distillation under reduced pressure to yield 10.0 g of N-[3-(4-chlorophenoxy)-2-hydroxypropyl]piperazine as a colorless oil.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture is refluxed
  3. stirringwith stirring for a further 1.5 hours
  4. concentrationconcentrated to dryness under reduced pressure
  5. dissolutionThe residue is dissolved in dilute hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. extractionextracted first with benzene from which there

Sources & evidence

ORD record
ord-4afb65a9d0d848589c11f3af3cdb6be0
Source dataset
uspto-grants-1981_05
Patent number
US04269838

Reaction notes

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