Reacción #943279

Ecuación de reacción

1-(4-trifluoromethoxyphenyl)-piperazine

2-(4-bromophenoxy)-tetrahydropyran

BINAP

sodium tert-butoxide

→

1-[4-(tetrahydropyran-2-yloxy)phenyl]-4-(4-trifluoromethoxyphenyl)piperazine

Rendimiento 35.9%

Disolventes

toluene

water

Ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed under a nitrogen atmosphere for 5 hours
2. 2
   OtroThe insoluble substances were removed by filtration through Celite
3. 3
   Extracciónthe filtrate was then extracted with ethyl acetate
4. 4
   LavadoThe extract was washed with brine
5. 5
   Secadodried over magnesium sulfate
6. 6
   Filtraciónfiltered
7. 7
   ConcentraciónThe filtrate was concentrated under reduced pressure
8. 8
   Otrothe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=20/1)

Procedimiento

A mixture of 1-(4-trifluoromethoxyphenyl)-piperazine (4.4 g, 17.8 mmol), 2-(4-bromophenoxy)-tetrahydropyran (4.6 g, 17.8 mmol), palladium acetate (159 mg, 0.71 mmol), BINAP (666 mg, 1.07 mmol) and sodium tert-butoxide (2.2 g, 23.1 mmol) in toluene (40 ml) was refluxed under a nitrogen atmosphere for 5 hours. Ethyl acetate and water were added to the reaction mixture, which was stirred for a while. The insoluble substances were removed by filtration through Celite, and the filtrate was then extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=20/1) to afford 1-[4-(tetrahydropyran-2-yloxy)phenyl]-4-(4-trifluoromethoxyphenyl)piperazine (2.7 g, yield 35%) as a white powder.

Fuente