Reacción #44051

Ecuación de reacción

Sodium carbonate

2-bromo-1-(3-nitrophenyl)ethanone

2-methyl-5-(1-piperazinyl)quinoline

2-Methyl-5-(1-piperazinyl)quinoline

NaBH4

→

title compound

Rendimiento 55.0%

1-(3-Aminophenyl)-2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethanol

Rendimiento 55.0%

Disolventes

tetrahydrofuran

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITthe reaction was left
2. 2
   workup.ADDITIONwas added
3. 3
   workup.WAITthe reaction was left
4. 4
   workup.STIRRINGunder stirring for 1 h
5. 5
   OtroThe solvent was removed under reduced pressure
6. 6
   OtroThe crude material was purified on SPE cartridge (SCX)

Procedimiento

Sodium carbonate (1.5 eq) and 2-bromo-1-(3-nitrophenyl)ethanone (1.5 eq) were added to a stirred solution of 2-methyl-5-(1-piperazinyl)quinoline (D3) (1 eq) in tetrahydrofuran at room temperature under an inert atmosphere, and the reaction was left under stirring for 1 h. The solution was then diluted with MeOH, NaBH4 (2 eq) was added and the reaction was left under stirring for 1 h. The solvent was removed under reduced pressure. The crude material was purified on SPE cartridge (SCX) using as eluant a gradient from MeOH to MeOH:CH2Cl2 (1:1) and then 2M NH3 in MeOH affording an intermediate which was reduced following a similar procedure to D6 to give the title compound in 55% yield.

Fuente