1-Methylpiperazine → Ethyl 1-ethyl-8-(4-methylpiperazin-1-yl)-6,7,9-trifluoro-4H-quinolizin-4-one-3-carboxylate

HRID 1080213Notes

Reaction equation

HRID 1080213 reaction equation
Cl[C:2]1(F)[C:11]([F:12])=[C:10]2[N:5]([C:6](=[O:20])[CH:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:8]=[C:9]2[CH2:13][CH3:14])[C:4]([F:21])=[C:3]1[F:22].[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>N1C=CC=CC=1>[CH2:13]([C:9]1[CH:8]=[C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:6](=[O:20])[N:5]2[C:10]=1[C:11]([F:12])=[C:2]([N:28]1[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]1)[C:3]([F:22])=[C:4]2[F:21])[CH3:14]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 131719739HCID 131719739, compound

Product 1

HCID 19691351Ethyl 1-ethyl-8-(4-methylpiperazin-1-yl)-6,7,9-trifluoro-4H-quinolizin-4-one-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
85 °C

Procedure

Ethyl 8-chloro-1-ethyl-6,7,8,9-tetrafluoro-4H-quinolizin-4-one-3-carboxylate (317 mg, 1.0 mmol), from Step 4, is dissolved in 5 mL of dry pyridine under a nitrogen atmosphere. To the resultant solution is added 2 mL (2.0 mmol) of N-methylpiperazine and the stirred reaction mixture is heated at 85° C. for 2.5 hours. The reaction mixture is allowed to cool to ambient temperature and then concentrated in vacuo in order to remove all of the pyridine. The residue is dissolved in 50 mL of methylene chloride and the methylene chloride solution is washed with 50 mL of 5% aqueous sodium bicarbonate solution. The aqueous layer is extracted with 3×50 mL of methylene chloride and the combined methylene chloride solutions are dried over anhydrous sodium sulfate, filtered and concentrated and dried in vacuo to afford the title compound.

Workup

  1. customthe stirred reaction mixture
  2. temperatureto cool to ambient temperature
  3. concentrationconcentrated in vacuo in order
  4. customto remove all of the pyridine
  5. dissolutionThe residue is dissolved in 50 mL of methylene chloride
  6. washthe methylene chloride solution is washed with 50 mL of 5% aqueous sodium bicarbonate solution
  7. extractionThe aqueous layer is extracted with 3×50 mL of methylene chloride
  8. dry with materialthe combined methylene chloride solutions are dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customdried in vacuo

Sources & evidence

ORD record
ord-f18a66e7bdca49358618e7ef1d3f0b03
Source dataset
uspto-grants-1996_12
Patent number
US05580872

Reaction notes

Loading…