Reacción #68123

Ecuación de reacción

N,N-dimethylformamide

ethyl 4-(3-(7-methoxy-2-oxo-1,2-dihydroquinolin-1-yl)propyl)piperidine-4-carboxylate

potassium carbonate

N,N-dimethylformamide

(2-bromoethoxy)benzene

→

ethyl 4-(3-(7-methoxy-2-oxo-1,2-dihydroquinolin-1-yl)propyl)-1-(2-phenoxyethyl)piperidine-4-carboxylate

Rendimiento 90.7%

Disolventes

ethyl acetate

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added at room temperature
2. 2
   workup.WAITto stand overnight
3. 3
   OtroThe organic layer was separated
4. 4
   Lavadowashed with aqueous saturated sodium chloride solution
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   Otrothe solvent was removed under reduced pressure
7. 7
   OtroThe residue thus obtained
8. 8
   Otrowas purified by silica gel column chromatography [eluent; chloroform:methanol=30:1]

Procedimiento

To 2 mL of an N,N-dimethylformamide solution containing 0.10 g of ethyl 4-(3-(7-methoxy-2-oxo-1,2-dihydroquinolin-1-yl)propyl)piperidine-4-carboxylate, 74 mg of potassium carbonate and 1 mL of an N,N-dimethylformamide solution containing 60 mg of (2-bromoethoxy)benzene were added at room temperature. After stirred at 50° C. for 30 min, it was allowed to stand overnight. To the reaction mixture, water and ethyl acetate were added. The organic layer was separated, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=30:1], to give 0.12 g of ethyl 4-(3-(7-methoxy-2-oxo-1,2-dihydroquinolin-1-yl)propyl)-1-(2-phenoxyethyl)piperidine-4-carboxylate as a yellow oil.

Fuente