Reacción #1949

Ecuación de reacción

Ethyl 8-chloro-1-ethyl-4H-quinolizin-4-one-3-carboxylate

N-methylpiperazine

→

title compound

Rendimiento 99.9%

Ethyl 1-ethyl-8-(4-methylpiperazin-1-yl)-4H-quinolizin-4-one-3-carboxylate

Rendimiento 99.9%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe stirred reaction mixture
2. 2
   Temperaturato cool to ambient temperature
3. 3
   Concentraciónconcentrated in vacuo in order
4. 4
   Otroto remove all of the pyridine
5. 5
   workup.DISSOLUTIONThe residue was dissolved in 50 mL of methylene chloride
6. 6
   Lavadothe methylene chloride solution was washed with 50 mL of 5% aqueous sodium bicarbonate solution
7. 7
   ExtracciónThe aqueous layer was extracted with 3 X 50 mL of methylene chloride
8. 8
   Secadothe combined methylene chloride solutions were dried over anhydrous sodium sulfate
9. 9
   Filtraciónfiltered
10. 10
    Concentraciónconcentrated
11. 11
    Otrodried in vacuo

Procedimiento

Ethyl 8-chloro-1-ethyl-4H-quinolizin-4-one-3-carboxylate (279 mg, 1.0 mmol), the product of Step 3 of Example 62, was dissolved in 5 mL of dry pyridine under a nitrogen atmosphere. To the resultant solution was added 2 mL (2.0 mmol) of N-methylpiperazine and the stirred reaction mixture was heated at 85° C. for 2.5 hours. The reaction mixture was allowed to cool to ambient temperature and then concentrated in vacuo in order to remove all of the pyridine. The residue was dissolved in 50 mL of methylene chloride and the methylene chloride solution was washed with 50 mL of 5% aqueous sodium bicarbonate solution. The aqueous layer was extracted with 3 X 50 mL of methylene chloride and the combined methylene chloride solutions were dried over anhydrous sodium sulfate, filtered and concentrated and dried in vacuo to afford 343 mg of the title compound, m.p. 94°-96° C.; MS DCI-NH3 : 344 (M+H)+.

Fuente