Reacción #77538

Ecuación de reacción

1-Bromo-7-(4-chlorophenoxy)heptane

1-(4-pyridyl)-2-imidazolidinone

NaH

→

Compound 2

1-[7-(4-chlorophenoxy)heptyl]-3-(4-pyridyl)-2-imidazolidinone

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled in an ice bath
2. 2
   Temperaturathen cooled in ice bath again
3. 3
   workup.STIRRINGthe mixture was stirred at room temperature for additional 4 hours
4. 4
   OtroThe reaction was quenched with methanol
5. 5
   Otrothe solvent was removed under reduced pressure
6. 6
   workup.ADDITION5 mL of saturated aqueous NH4Cl solution and 10 mL dichloromethane were successively added to the residue
7. 7
   OtroThe dichloromethane layer was separated
8. 8
   Secadodried over MgSO4
9. 9
   Filtraciónfiltered
10. 10
    Otroevaporated
11. 11
    Otropurified by column chromatography (ethyl acetate:MeOH=10:1)

Procedimiento

To a solution of 1-(4-pyridyl)-2-imidazolidinone (0.10 g, 0.62 mmol) dissolved in 10 mL dimethylformamide cooled in an ice bath was added NaH (60% dispersion in mineral oil, 27.2 mg, 0.68 mmol). The mixture was stirred at room temperature for 30 minutes then cooled in ice bath again. 1-Bromo-7-(4-chlorophenoxy)heptane (0.19 g, 0.62 mmol) was added, and the mixture was stirred at room temperature for additional 4 hours. The reaction was quenched with methanol, and the solvent was removed under reduced pressure. 5 mL of saturated aqueous NH4Cl solution and 10 mL dichloromethane were successively added to the residue. The dichloromethane layer was separated and dried over MgSO4, filtered, evaporated, and purified by column chromatography (ethyl acetate:MeOH=10:1) to give the product (i.e., Compound 2) as a white solid (0.15 g, 62%).

Fuente