Potassium Carbonate → pyridinylpiperazine ethyl-1H-isoindole-1,3(2H)-dione

HRID 470328Notes

Reaction equation

HRID 470328 reaction equation
[N:1]1[C:10]2[C:9]3C=CC=C[C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=[N:3][C:2]=1[OH:15].Cl[C:17]1[N:26]=[CH:25][C:24]2[CH2:23][CH2:22]C3C=C(OC)C=C[C:20]=3[C:19]=2[N:18]=1.C(=O)([O-])[O-:34].[K+].[K+]>C(#N)C>[CH2:19]([N:3]1[C:2](=[O:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=[O:34])[CH3:24].[N:26]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[N:18]1[CH2:19][CH2:20][NH:1][CH2:10][CH2:5]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53486023HCID 53486023, compoundHCID 1785175485,6-Dihydrobenzo[h]quinazolin-2-ol

Product 1

HCID 67058601pyridinylpiperazine ethyl-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of bromoethyl phthalimide 1 (5 mmol) and 2-pyridyl piperazine 2 (5 mmol) in acetonitrile (10 mL) was added potassium carbonate (0.690 g, 5 mmol) and resulting reaction mixture was stirred under reflux. After completion of the reaction, solvent was removed on rotavap and residue was dissolved in chloroform (20 mL). Then washed with water (5 mL) and saturated sodium bicarbonate solution (5 mL), dried over anhydrous sodium sulfate. Filtered and evaporation of solvent gave pyridinylpiperazine ethyl-1H-isoindole-1,3(2H)-dione. Then dissolved in methanol (10 mL), hydrazine hydrate (0.48 mL, 15 mmol) was added and stirred under reflux to give a precipitate. Filtered, washed with methanol (5 mL) and evaporation of solvent gave 2-(4-pyridin-2-ylpiperazin-1-yl)ethanamine 3 which was used as such in the next step.

Workup

  1. customresulting
  2. customreaction mixture
  3. temperatureunder reflux
  4. customAfter completion of the reaction, solvent
  5. customwas removed on rotavap
  6. dissolutionresidue was dissolved in chloroform (20 mL)
  7. washThen washed with water (5 mL) and saturated sodium bicarbonate solution (5 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationFiltered
  10. customevaporation of solvent

Sources & evidence

ORD record
ord-3b10dbd18b7e4cf482b7de47818bc2bc
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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