1-(2-Methoxyphenyl)piperazine → 2-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]isoindole-1,3-dione

HRID 1251317Notes

Reaction equation

HRID 1251317 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.Br[CH2:16][CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:16][CH2:17][N:18]2[C:22](=[O:23])[C:21]3=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]3[C:19]2=[O:28])[CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium Carbonate

Product 1

HCID 86874532-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]isoindole-1,3-dioneYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 1-(2-methoxyphenyl)piperazine (41.2 mmol) in 100 mL of acetonitrile and 12 mL of dimethylformamide was combined with N-(2-bromoethyl)phthalimide (43.3 mmol) and potassium carbonate (61.8 mmol). The mixture was heated to reflux for 8 hours. After cooling, the reaction mixture was quenched with water, extracted with dichloromethane. The organic phase was washed with brine, water, and dried over magnesium sulfate. Filtration and evaporation of the solvents gave a yellow oily residue that was purified by flash chromatography using hexanes and ethyl acetate (1:1) to give 1-(2-methoxyphenyl)-4-[(2-phthalimido)ethyl]piperazine (8.56 g, 57%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 8 hours
  3. temperatureAfter cooling
  4. customthe reaction mixture was quenched with water
  5. extractionextracted with dichloromethane
  6. washThe organic phase was washed with brine, water
  7. dry with materialdried over magnesium sulfate
  8. filtrationFiltration and evaporation of the solvents
  9. customgave a yellow oily residue that
  10. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-98b16d636dde454483cec7188a9f30fa
Source dataset
uspto-grants-2002_01
Patent number
US06342498B1

Reaction notes

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