Reacción #2613

Ecuación de reacción

sodium iodide

4-nitro-N-(3-pyridyl)benzamide

sodium hydride

sodium chloride

1-(2-chloroethyl)-4-benzoylpiperidine

→

title compound

Rendimiento 24.0%

4-Nitro-N-[2-(4-benzoyl-1-piperidinyl)ethyl]-N-(3-pyridyl)benzamide

Rendimiento 24.0%

Disolventes

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat room temperature
2. 2
   workup.STIRRINGAfter 4 hours of stirring at 60° C.
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   LavadoThe resulting organic layer was washed with saturated sodium chloride aqueous solution and water in that order
5. 5
   Secadodried on anhydrous sodium sulfate
6. 6
   OtroThereafter, the solvent was removed by evaporation
7. 7
   Otrothe resulting residue was purified by recrystallization (ethyl acetate-ether)

Procedimiento

In an atmosphere of argon, 4-nitro-N-(3-pyridyl)benzamide (973 mg, 4.00 mmol) was dissolved in DMF (10 ml) to which was subsequently added sodium hydride (176 mg, 60%, 4.40 mmol) at room temperature, stirred for 1 hour at 60° C., and added dropwise 1-(2-chloroethyl)-4-benzoylpiperidine (1.38 g, 5.49 mmol) and a catalytically effective amount of a DMF solution (12 ml) of sodium iodide. After 4 hours of stirring at 60° C., the reaction solution was mixed with saturated sodium chloride aqueous solution and extracted with ethyl acetate. The resulting organic layer was washed with saturated sodium chloride aqueous solution and water in that order, and dried on anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by recrystallization (ethyl acetate-ether) to obtain 439.6 mg (24.0%) of the title compound in a light yellow powder form.

Fuente