Hydrochloric Acid → HCID 12899685, compound

HRID 1649437Notes

Reaction equation

HRID 1649437 reaction equation
Cl[C:2]1[C:13]2=[C:14]3[N:9]([CH2:10][CH2:11][CH2:12]2)[CH:8]=[C:7]([C:15]([OH:17])=[O:16])[C:6](=[O:18])[C:5]3=[CH:4][CH:3]=1.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.Cl>CS(C)=O>[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([C:2]2[C:13]3=[C:14]4[N:9]([CH2:10][CH2:11][CH2:12]3)[CH:8]=[C:7]([C:15]([OH:17])=[O:16])[C:6](=[O:18])[C:5]4=[CH:4][CH:3]=2)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 531671-MethylpiperazineHCID 12899682HCID 12899682, compound

Product 1

HCID 12899685HCID 12899685, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4.0 g of 8-chloro-6,7-dihydro-1-oxo-1H,5H-benzo-[ij]quinolizine-2-carboxylic acid and 4.6 g of N-methylpiperazine was added to 10 ml of anhydrous dimethylsulfoxide and the mixture was heated on an oil bath at 150° to 160° C. for 8 hours while stirring. After completion of the reaction, the solvent and excessive methylpiperazine were removed under reduced pressure and a mixture of methanol and diethyl ether was added to form precipitates which were separated by filtration and washed with diethyl ether. The crystals thus obtained were suspended in 20 ml of a 10% aqueous hydrochloric acid solution and insoluble materials were removed by filtration. The filtrate was purified through column chromatography using Amberlite LH-20 (a trade name for a product of Tokyo Organic Chemical Industries Ltd.) (eluent: water, ethanol). Recrystallization of the eluate from dimethylformamide gave 1.0 g of 8-(4-methyl-1-piperazinyl)-6,7-dihydro-1-oxo-1H,5H-benzo-[ij]quinolizine-2-carboxylic acid light yellow plates having a melting point of 278° to 280.5° C.

Workup

  1. temperaturethe mixture was heated on an oil bath at 150° to 160° C. for 8 hours
  2. customAfter completion of the reaction
  3. customthe solvent and excessive methylpiperazine were removed under reduced pressure
  4. additiona mixture of methanol and diethyl ether
  5. additionwas added
  6. customto form
  7. customprecipitates which
  8. customwere separated by filtration
  9. washwashed with diethyl ether
  10. customThe crystals thus obtained
  11. customwere removed by filtration
  12. customThe filtrate was purified through column chromatography
  13. customRecrystallization of the eluate from dimethylformamide

Sources & evidence

ORD record
ord-693084d2fcf944eab2e4444689eaf813
Source dataset
uspto-grants-1983_11
Patent number
US04416884

Reaction notes

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