Réaction #1963

Équation de réaction

Ethyl 8-chloro-7-fluoro-1-methylamino-4H-quinolizin-4-one-3-carboxylate

product

Ethyl 8-chloro-7-fluoro-1-methylamino-4H-quinolizin-4-one-3-carboxylate

N-methylpiperazine

→

title compound

Ethyl 7-fluoro-1-methylamino-8-(4-methylpiperazin-1-yl)-4H-quinolizin-4-one-3-carboxylate

Solvants

pyridine

Conditions de réaction

Traitement

1. 1
   ConcentrationThe reaction mixture is then concentrated in vacuo in order
2. 2
   Autreto remove all of the pyridine
3. 3
   workup.DISSOLUTIONThe dry residue is dissolved in 125 mL of methylene chloride
4. 4
   Lavagethe methylene chloride solution is washed with 125 mL of brine
5. 5
   ExtractionThe aqueous layer is extracted with 125 mL of methylene chloride
6. 6
   Séchagethe combined methylene chloride solutions are dried over anhydrous sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated
9. 9
   Autredried in vacuo

Mode opératoire

Ethyl 8-chloro-7-fluoro-1-methylamino-4H-quinolizin-4-one-3-carboxylate (899 mg, 3.0 mmol), the product of Step 6, is suspended in 12 mL of dry pyridine under a nitrogen atmosphere. To the resultant solution is added 6.0 mL (6.0 mmol) of N-methylpiperazine and the reaction mixture is heated at 70° C. for 8 hours. The reaction mixture is then concentrated in vacuo in order to remove all of the pyridine. The dry residue is dissolved in 125 mL of methylene chloride and the methylene chloride solution is washed with 125 mL of brine. The aqueous layer is extracted with 125 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