Reacción #1736636

Ecuación de reacción

8,9-dichloro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

1-propargylpiperazine

→

8-[4-(2-propynyl)-1-piperazinyl]-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

Rendimiento 58.5%

Disolventes

HMPTA

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   OtroAfter completion of the reaction
3. 3
   Otrothe solvent was removed by distillation
4. 4
   Lavadothe residue was washed with water
5. 5
   workup.DISSOLUTIONThe residue was dissolved in 100 ml of water
6. 6
   Otroinsoluble substances were removed by filtration
7. 7
   ExtracciónThe aqueous fraction was extracted with 200 ml of chloroform
8. 8
   Secadothe chloroform fraction was dried over anhydrous sodium sulfate
9. 9
   ConcentraciónAfter concentration
10. 10
    Otrothe concentrate was purified through a silica gel column chromatography (silica gel

Procedimiento

A mixture of 1.6 g of 8,9-dichloro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 3.2 g of 1-propargylpiperazine and 25 ml of HMPTA was heated with stirring at 160° C. for 5 hours under atmosphere of argon. After completion of the reaction, the solvent was removed by distillation and the residue was washed with water. The residue was dissolved in 100 ml of water and insoluble substances were removed by filtration. The aqueous fraction was extracted with 200 ml of chloroform and the chloroform fraction was dried over anhydrous sodium sulfate. After concentration, the concentrate was purified through a silica gel column chromatography (silica gel: Wako C-200, a trade name for a product of Wako Junyako Co., Ltd.; eluent: chloroform-methanol (9:1 by volume)) to obtain 1.2 g of 8-[4-(2-propynyl)-1-piperazinyl]-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid having a melting point of 211° to 213° C.

Fuente