Reacción #2271683

Ecuación de reacción

acetonitrile

6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole

1-[4-(3-chloropropoxy)-3-methoxyphenyl]-2,2,2-trifluoroethanone

K2CO3

→

1-[4-[3-[4- (6-fluoro-1,2-benzisoxazol-3-yl)-1- piperidinyl]-propoxy]-3-methoxyphenyl]-2,2,2-trifluoroethanone

Rendimiento 56.0%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturarefluxed for 16 hours
2. 2
   TemperaturaAfter cooling
3. 3
   Extracciónthe aqueous mixture extracted with ethyl acetate
4. 4
   LavadoThe extract was washed (H2O)
5. 5
   Secadodried (MgSO4)
6. 6
   Concentraciónthe solvent was concentrated to an oil, which upon evacuation at high vacuum
7. 7
   Otroafforded 3.2 g of a waxy solid
8. 8
   OtroThe solid was chromatographed on a Waters preparative LC (silica columns, eluting with methanol-dichloromethane)

Procedimiento

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (1.5 g, 6.7 mmol), 1-[4-(3-chloropropoxy)-3-methoxyphenyl]-2,2,2-trifluoroethanone (2.0 g, 6.7 mmol). K2CO3 (0.88 g). Kl (0.1 g) and acetonitrile (50 ml.) was stirred and refluxed for 16 hours. After cooling, the reaction was poured into water and the aqueous mixture extracted with ethyl acetate. The extract was washed (H2O), dried (MgSO4), and the solvent was concentrated to an oil, which upon evacuation at high vacuum afforded 3.2 g of a waxy solid. The solid was chromatographed on a Waters preparative LC (silica columns, eluting with methanol-dichloromethane). Concentration of the appropriate fractions gave 1.8 g (56%) of 1-[4-[3-[4- (6-fluoro-1,2-benzisoxazol-3-yl)-1- piperidinyl]-propoxy]-3-methoxyphenyl]-2,2,2-trifluoroethanone solid, m.p.=94°-96° C.

Fuente