Piperazine → HCID 12836921, compound

HRID 2058505Notes

Reaction equation

HRID 2058505 reaction equation
[Cl:1][C:2]1[C:11]2[CH2:12][CH2:13][N:9]3[C:10]=2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8]3)=[CH:4][CH:3]=1.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>CS(C)=O>[ClH:1].[N:18]1([C:2]2[C:11]3[CH2:12][CH2:13][N:9]4[C:10]=3[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8]4)=[CH:4][CH:3]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 12836918HCID 12836918, compound

Product 1

HCID 12836921HCID 12836921, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

20 ml of dimethyl sulfoxide were added to a mixture of 3 g of 9-chloro-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid and 6 g of anhydrous piperazine and the mixture was heated on an oil bath at 140° to 150° C. for 6 hours. After completion of reaction, the solvent was removed therefrom under reduced pressure and 50 ml of water was added to the residue to dissolve it. The solution was shaken with 100 ml of chloroform and the water layer was separated and treated with activated carbon. The aqueous solution was rendered acidic with a 10% aqueous hydrochloric acid and filtered. The filtrate was again treated with activated carbon followed by concentration. The addition of ethanol to the concentrate gave rise to crystals which were recrystallized from ethanol-water to obtain 1.5 g of 9-(1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride as light yellow needles having a melting point of 300° C. or more.

Workup

  1. temperaturethe mixture was heated on an oil bath at 140° to 150° C. for 6 hours
  2. customAfter completion of reaction
  3. customthe solvent was removed
  4. additionunder reduced pressure and 50 ml of water was added to the residue
  5. dissolutionto dissolve it
  6. customthe water layer was separated
  7. additiontreated with activated carbon
  8. filtrationfiltered
  9. additionThe filtrate was again treated with activated carbon
  10. concentrationfollowed by concentration
  11. additionThe addition of ethanol to the concentrate
  12. customgave rise to crystals which
  13. customwere recrystallized from ethanol-water

Sources & evidence

ORD record
ord-a363df6095454a7c9f68b305254f65ff
Source dataset
uspto-grants-1982_03
Patent number
US04317820

Reaction notes

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