1-Phenylpiperazine → HCID 23345032, compound

HRID 1856455Notes

Reaction equation

HRID 1856455 reaction equation
[O:1]1[CH2:19][CH:2]1[CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:13]2[CH2:17][NH:16][C:15](=[O:18])[CH2:14]2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].[C:20]1([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO>[CH3:12][O:11][C:10]1[CH:9]=[CH:8][C:7]([CH:13]2[CH2:17][NH:16][C:15](=[O:18])[CH2:14]2)=[CH:6][C:5]=1[O:4][CH2:3][CH:2]([OH:1])[CH2:19][N:29]1[CH2:30][CH2:31][N:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 70961-PhenylpiperazineHCID 23345057HCID 23345057, compound

Product 1

HCID 23345032HCID 23345032, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

15.5 millimoles of 4-[3-(2,3-epoxypropoxy)-4-methoxyphenyl]-2-pyrrolidone is dissolved in 50 ml. of methanol. After the addition of 15.5 mmol of 1-phenylpiperazine (95% strength), the reaction mixture is heated for 3 hours under reflux. After cooling of the reaction solution, the solvent is removed under vacuum at 40°. The residue is taken up in 50 ml. of 1N hydrochloric acid and extracted twice with 100 ml. of chloroform. The aqueous phase is adjusted to be alkaline with 2N sodium hydroxide solution and thereafter extracted three times with ethyl acetate. The combined ethyl acetate phase are washed with saturated sodium chloride solution, and the solvent, after drying over sodium sulfate, is distilled off under vacuum. The residue is recrystallized from ethanol, thus obtaining in a 61% yield 4-{4-methoxy-3-[3-(4-phenylpiperazin-1-yl)-2-hydroxypropoxy ]phenyl}-2-pyrrolidone, m.p. 143°-144°.

Workup

  1. temperaturethe reaction mixture is heated for 3 hours
  2. temperatureunder reflux
  3. temperatureAfter cooling of the reaction solution
  4. customthe solvent is removed under vacuum at 40°
  5. extractionof 1N hydrochloric acid and extracted twice with 100 ml
  6. extractionextracted three times with ethyl acetate
  7. washThe combined ethyl acetate phase are washed with saturated sodium chloride solution
  8. dry with materialthe solvent, after drying over sodium sulfate
  9. distillationis distilled off under vacuum
  10. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-5f2da4f80fcf4f1c803468463369e82f
Source dataset
uspto-grants-1980_08
Patent number
US04219551

Reaction notes

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