Potassium Carbonate → 2-[3-(4-Methylpiperazin-1-yl)propyl]-1H-isoindole-1,3(2H)-dione

HRID 325893Notes

Reaction equation

HRID 325893 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].[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([CH2:2][CH2:3][CH2:4][N:5]2[C:9](=[O:10])[C:8]3=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]3[C:6]2=[O:15])[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 531671-Methylpiperazine

Product 1

HCID 202494272-[3-(4-Methylpiperazin-1-yl)propyl]-1H-isoindole-1,3(2H)-dioneYield 116.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the solution of N-(3-bromopropyl)phthalimide (402 g) in acetone (2.5 l) were added 1-methylpiperazine (225 g) and potassium carbonate (415 g). The resulting mixture was refluxed with stirring for 3.5 hours. The reaction mixture was cooled and then filtered. The filter cake was washed with acetone (500 ml). The filtrate and washing were combined and evaporated under reduced pressure. The remaining starting materials in the residnal oil were azeotropically removed with benzene to give an oil of N-[3-(4-methyl-1-piperazinyl)propyl]phthalimide (502 g). I.R. (Film): 1770,1700 cm-.

Workup

  1. temperatureThe resulting mixture was refluxed
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. washThe filter cake was washed with acetone (500 ml)
  5. washThe filtrate and washing
  6. customevaporated under reduced pressure
  7. customThe remaining starting materials in the residnal oil were azeotropically removed with benzene

Sources & evidence

ORD record
ord-eab356ab6038425791b39a88aad9dbc0
Source dataset
uspto-grants-1984_04
Patent number
US04443443

Reaction notes

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