1-Phenylpiperazine → 4-[4-methoxy-3-[2-(4-phenyl-1-piperazinyl)ethoxy]phenyl]pyrrolidin-2-one

HRID 1856458Notes

Reaction equation

HRID 1856458 reaction equation
Cl[CH2:2][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:19]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>CN(C)C=O>[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][CH2:2][N:28]1[CH2:29][CH2:30][N:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 23345044HCID 23345044, compound

Product 1

HCID 30184524-[4-methoxy-3-[2-(4-phenyl-1-piperazinyl)ethoxy]phenyl]pyrrolidin-2-oneYield 15.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20 mmol of 4-[3-(2-chloroethoxy)-4-methoxyphenyl]-2-pyrrolidone is dissolved in 50 ml. of dimethylformamide. After adding 22 mmol of 1-phenylpiperazine (95% strength) and 20 mmol of triethylamine, the reaction mixture is heated for 6 hours to 100 ° C. After the reaction has ceased, the solvent is withdrawn at 40° under a high vacuum. The residue is taken up in 50 ml. of ethyl acetate, washed with semisaturated sodium chloride solution, and the solvent, after drying over sodium sulfate, is distilled off under vacuum, thus obtaining in a 15.2% yield 4-{4-methoxy-3-[2-(4-phenylpiperazin-1-yl)ethoxy]-phenyl}-2-pyrrolidone, m.p. 140°-141°. The dihydrochloride, m.p. 219°-221°, is precipitated from ethereal hydrochloric acid.

Workup

  1. temperaturethe reaction mixture is heated for 6 hours to 100 ° C
  2. customthe solvent is withdrawn at 40° under a high vacuum
  3. washof ethyl acetate, washed with semisaturated sodium chloride solution
  4. dry with materialthe solvent, after drying over sodium sulfate
  5. distillationis distilled off under vacuum

Sources & evidence

ORD record
ord-023b593912de4be9a2dbb5527d61848f
Source dataset
uspto-grants-1980_08
Patent number
US04219551

Reaction notes

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