Reaktion #77538

Reaktionsgleichung

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

1-(4-pyridyl)-2-imidazolidinone

NaH

→

Compound 2

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

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled in an ice bath
2. 2
   Temperaturthen cooled in ice bath again
3. 3
   workup.STIRRINGthe mixture was stirred at room temperature for additional 4 hours
4. 4
   SonstigeThe reaction was quenched with methanol
5. 5
   Sonstigethe 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
   SonstigeThe dichloromethane layer was separated
8. 8
   Trocknendried over MgSO4
9. 9
   Filtrationfiltered
10. 10
    Sonstigeevaporated
11. 11
    Sonstigepurified by column chromatography (ethyl acetate:MeOH=10:1)

Vorschrift

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%).

Quelle