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

HRID 1714796Notes

Reaction equation

HRID 1714796 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>[NH2:20][CH2:19][CH2:18][CH2:17][N:14]1[CH2:15][CH2:16][N:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH2:12][CH2:13]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 30 ml of ethanol, 1.52 g of 2-[3-(4-quinolin-2-ylpiperazin-1-yl) propyl]isoindol-1,3-dione (a compound shown in Pol. J. Chem., 75, 71-78 (2001)) was added, followed by addition of 1.50 g of hydrazine monohydrate as dissolved in 10 ml of ethanol and 7 hours' heating under reflux. After cooling the reaction system, insoluble matter was removed by filtration and the solvent was distilled off under reduced pressure. After being rendered to alkaline with 5N sodium hydroxide, the residue was extracted with chloroform, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to provide 0.99 g (96%) of 2-[4-(3-aminopropyl)piperazin-1-yl]quinoline.

Workup

  1. addition, 75, 71-78 (2001)) was added
  2. temperatureheating
  3. temperatureunder reflux
  4. temperatureAfter cooling the reaction system, insoluble matter
  5. customwas removed by filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. extractionthe residue was extracted with chloroform
  8. washwashed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-81ecd41cfd6a4f8ea83ef49b5bc80231
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

Loading…