1-Methylpiperazine → HCID 13188590, compound

HRID 851086Notes

Reaction equation

HRID 851086 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]2[O:9][CH2:8][CH:7]([CH3:10])[N:6]3[CH:11]=[C:12]([C:17]([OH:19])=[O:18])[C:13](=[O:16])[C:14]([CH:15]=1)=[C:5]23.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CS(C)=O>[Cl:1][C:2]1[C:3]([N:25]2[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]2)=[C:4]2[O:9][CH2:8][CH:7]([CH3:10])[N:6]3[CH:11]=[C:12]([C:17]([OH:19])=[O:18])[C:13](=[O:16])[C:14]([CH:15]=1)=[C:5]23

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 13188589HCID 13188589, compound

Product 1

HCID 13188590HCID 13188590, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

150 mg (0.5 mmol) of 9-chloro-10-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid was suspended in 3 ml of dimethyl sulfoxide and 150 mg of N-methylpiperazine was added to the suspension. The mixture was then allowed to react at 120°-130° C. (bath temperature) for 6 hours. After cooling, the solvent was distilled off under reduced pressure and the residue was washed with diethyl ether to remove any insoluble substance. The resulting residue was purified by silica gel (7 g) column chromatography using methanol-chloroform (5:95 by volume) and then methanol-chloroform (10:90 by volume) as eluants, and the resulting product was recrystallized from ethanol to provide 65 mg (34.4% yield) of 9-chloro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid as pale yellow fine needles with m.p. 275°-276° C. (with decomposition).

Workup

  1. customto react at 120°-130° C. (bath temperature) for 6 hours
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled off under reduced pressure
  4. washthe residue was washed with diethyl ether
  5. customto remove any insoluble substance
  6. customThe resulting residue was purified by silica gel (7 g) column chromatography
  7. custommethanol-chloroform (10:90 by volume) as eluants, and the resulting product was recrystallized from ethanol

Sources & evidence

ORD record
ord-7cbb874317f545d59d0614be714b3b59
Source dataset
uspto-grants-1983_05
Patent number
US04382892

Reaction notes

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