Hydrazine hydrate (1:1) → HCID 21287994, compound

HRID 1714777Notes

Reaction equation

HRID 1714777 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][N:20]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:13][CH2:12]1.O.NN>C(O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH2:19][NH2:20])[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 23155617HCID 23155617, compound

Product 1

HCID 21287994HCID 21287994, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 1.52 g of 2-[3-(4-quinolin-2-ylpiperazin-1-yl)propyl]isoindol-1,3-dione in 30 ml of ethanol, another solution of 1.50 g of hydrazine monohydrate in 10 ml of ethanol was added, and heated under reflux for 7 hours. Cooling the reaction mixture, insoluble matter was separated by filtration, and the solvent was distilled off under reduced pressure. The residue was made alkaline with 5N-sodium hydroxide, extracted with chloroform, washed with saturated brine and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, 0.99 g (96%) of 3-(4-quinolin-2-ylpiperazin-1-yl)propylamine was obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 7 hours
  3. temperatureCooling the reaction mixture, insoluble matter
  4. customwas separated by filtration
  5. distillationthe solvent was distilled off under reduced pressure
  6. extractionextracted with chloroform
  7. washwashed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-ca60ead481994f1b84b62a6fa8080d54
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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