Réaction #1967

Équation de réaction

Ethyl 8-chloro-1-ethyl-6,7,8,9-tetrafluoro-4H-quinolizin-4-one-3-carboxylate

N-methylpiperazine

→

title compound

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

Solvants

pyridine

Conditions de réaction

Traitement

1. 1
   Autrethe stirred reaction mixture
2. 2
   Températureto cool to ambient temperature
3. 3
   Concentrationconcentrated in vacuo in order
4. 4
   Autreto remove all of the pyridine
5. 5
   workup.DISSOLUTIONThe residue is dissolved in 50 mL of methylene chloride
6. 6
   Lavagethe methylene chloride solution is washed with 50 mL of 5% aqueous sodium bicarbonate solution
7. 7
   ExtractionThe aqueous layer is extracted with 3 X 50 mL of methylene chloride
8. 8
   Séchagethe combined methylene chloride solutions are dried over anhydrous sodium sulfate
9. 9
   Filtrationfiltered
10. 10
    Concentrationconcentrated
11. 11
    Autredried in vacuo

Mode opératoire

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 X 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.

Source