1-Methylpiperazine → HCID 13520243, compound

HRID 485084Notes

Reaction equation

HRID 485084 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.F[C:9]1[C:20]2=[C:21]3[N:16]([C:17](=[CH2:22])[CH2:18][CH2:19]2)[CH:15]=[C:14]([C:23]([OH:25])=[O:24])[C:13](=[O:26])[C:12]3=[CH:11][C:10]=1[F:27]>CS(C)=O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:9]2[C:20]3=[C:21]4[N:16]([C:17](=[CH2:22])[CH2:18][CH2:19]3)[CH:15]=[C:14]([C:23]([OH:25])=[O:24])[C:13](=[O:26])[C:12]4=[CH:11][C:10]=2[F:27])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 13373748HCID 13373748, compound

Product 1

HCID 13520243HCID 13520243, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

400 mg of N-methylpiperazine and 6 ml of dimethyl sulfoxide were added to 400 mg of 8,9-difluoro-5-methylene-6,7-dihydro-1-oxo-1H,5H-benzo(ij)quinolizine-2-carboxylic acid and the resulting mixture was heated for 2.5 hours at 100°-110° C. (bath temperature). The solvent was distilled off in vacuo and water was added to the residue. The mixture was extracted with chloroform and the extract was dried. The solvent was distilled off and the residue was purified by silica gel column chromatography and then recrystallized from ethanol to give 85 mg of 8-(4-methyl-1-piperazinyl)-9-fluoro-5-methylene-6,7-dihydro-1-oxo-1H,5H-benzo(ij)quinolizine-2-carboxylic acid as microcrystals with 282°-285° C. (decomposition).

Workup

  1. temperaturethe resulting mixture was heated for 2.5 hours at 100°-110° C. (bath temperature)
  2. distillationThe solvent was distilled off in vacuo and water
  3. additionwas added to the residue
  4. extractionThe mixture was extracted with chloroform
  5. customthe extract was dried
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by silica gel column chromatography
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-23e023c15f504d9d83ce3c5db2c3b6fb
Source dataset
uspto-grants-1985_08
Patent number
US04535161

Reaction notes

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