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

HRID 470328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 470328
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3b10dbd18b7e4cf482b7de47818bc2bc
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629147B2

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