Hydrochloric Acid → HCID 12899683, compound

HRID 1649439Notes

Reaction equation

HRID 1649439 reaction equation
C1(C)C=CC(S([C:10]2[C:21]3=[C:22]4[N:17]([CH2:18][CH2:19][CH2:20]3)[CH:16]=[C:15]([C:23]([OH:25])=[O:24])[C:14](=[O:26])[C:13]4=[CH:12][CH:11]=2)(=O)=O)=CC=1.[NH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.CS(C)=O.Cl>O>[N:28]1([C:10]2[C:21]3=[C:22]4[N:17]([CH2:18][CH2:19][CH2:20]3)[CH:16]=[C:15]([C:23]([OH:25])=[O:24])[C:14](=[O:26])[C:13]4=[CH:12][CH:11]=2)[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 4837PiperazineHCID 20479717HCID 20479717, compound

Product 1

HCID 12899683HCID 12899683, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

19.1 g of 8-(p-toluenesulfonyl)-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid and 12.9 g of piperazine were added to 200 ml of anhydrous dimethyl sulfoxide and the mixture was heated in an autoclave under flow of nitrogen at 10 atm. at a temperature of 150° to 160° C. for 18 hours while stirring. After completion of the reaction, the solvent and excess piperazine were removed under reduced pressure and a mixture of methanol and ethanol was added to the residue. The preicpitates formed were separated by filtration and washed with diethyl ether. The crystals thus-obtained were suspended in a mixture of 200 ml of water and 40 ml of a 10% aqueous hydrochloric acid solution and insoluble materials were removed by filtration. The filtrate was rendered neutral with saturated aqueous solution of sodium bicarbonate and 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 2.7 g of 8-(1-piperazinyl)-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid as white needles having a melting point of 267° to 268° C.

Workup

  1. temperaturethe mixture was heated in an autoclave under flow of nitrogen at 10 atm. at a temperature of 150° to 160° C. for 18 hours
  2. customAfter completion of the reaction
  3. customthe solvent and excess piperazine were removed under reduced pressure
  4. additiona mixture of methanol and ethanol
  5. additionwas added to the residue
  6. customThe preicpitates formed
  7. customwere separated by filtration
  8. washwashed with diethyl ether
  9. customThe crystals thus-obtained
  10. customwere removed by filtration
  11. custompurified through column chromatography
  12. customRecrystallization of the eluate from dimethylformamide

Sources & evidence

ORD record
ord-1583609fec9d4e98bc2ec34d2737f8c5
Source dataset
uspto-grants-1983_11
Patent number
US04416884

Reaction notes

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