1-Phenylpiperazine → 2-[3-(4-Phenyl-piperazin-1-yl)-propyl]-isoindole-1,3-dione

HRID 325904Notes

Reaction equation

HRID 325904 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].[C:16]1([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:16]1([N:22]2[CH2:27][CH2:26][N:25]([CH2:2][CH2:3][CH2:4][N:5]3[C:9](=[O:10])[C:8]4=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]4[C:6]3=[O:15])[CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 21611N-3-Bromopropylphthalimide

Product 1

HCID 64248092-[3-(4-Phenyl-piperazin-1-yl)-propyl]-isoindole-1,3-dioneYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the solution of N-(3-bromopropyl)phthalimide (15.6 g) in acetone (150 ml) were added 1-phenylpiperazine (10.4 g) and potassium carbonate (12.0 g). The resulting mixture was refluxed with stirring for 4.5 hours. The reaction mixture was cooled and then filtered. The filter cake was washed with acetone. The filtrate and washing were combined and evaporated under reduced pressure. The residue was recrystallized from ethanol to give an oil of N-[3-(4-phenyl-1-piperazinyl)propyl]phthalimide (18.3 g), mp 129° to 134° C.

Workup

  1. temperatureThe resulting mixture was refluxed
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. washThe filter cake was washed with acetone
  5. washThe filtrate and washing
  6. customevaporated under reduced pressure
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-9d2caa01904a4a08aba6a2bcba2bbbb4
Source dataset
uspto-grants-1984_04
Patent number
US04443443

Reaction notes

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