Reacción #66530

Ecuación de reacción

HCl

dioxane

tert-butyl 4-(2-chloro-4-(picolinamido)phenyl)piperazine-1-carboxylate

→

N-(3-chloro-4-(piperazin-1-yl)phenyl)picolinamide

Rendimiento 40.0%

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter evaporation, DCM
2. 2
   workup.ADDITIONwas added
3. 3
   ExtracciónThe aqueous phase was extracted with DCM
4. 4
   LavadoThe organic phase was washed with brine
5. 5
   Secadowas dried over MgSO4
6. 6
   Filtraciónwas filtered
7. 7
   Concentraciónwas concentrated under reduced pressure
8. 8
   OtroThe crude product was purified by flash chromatography over silica gel

Procedimiento

According to Scheme 5 Step 4: HCl 4 M in dioxane (12.3 mmol, 3.07 mL) was added to a solution of tert-butyl 4-(2-chloro-4-(picolinamido)phenyl)piperazine-1-carboxylate (2.46 mmol, 1.02 g) in DCM (10 mL). The reaction mixture was stirred at room temperature overnight. After evaporation, DCM was added and then a NaOH 1 M solution. The aqueous phase was extracted with DCM. The organic phase was washed with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel using cyclohexane/AcOEt (60:40) as eluent to afford N-(3-chloro-4-(piperazin-1-yl)phenyl)picolinamide (0.97 mmol, 308 mg, 40%) as an orange solid.

Fuente