Reacción #2271670

Ecuación de reacción

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

K2CO3

1-[4-(4-bromobutoxy)-3-methoxyphenyl]ethanone

dimethylformamide

→

product

Rendimiento 87.4%

1-[4-[4-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]butoxy]-3-methoxyphenyl]ethanone

Rendimiento 87.4%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe aqueous mixture was extracted with ethyl acetate
2. 2
   LavadoThe ethyl acetate was washed (water)
3. 3
   Secadodried (MgSO4)
4. 4
   Concentraciónthe solvent was concentrated
5. 5
   Otroto yield initially an oil, which
6. 6
   OtroThe solid was triturated with hexane
7. 7
   Otrocollected

Procedimiento

A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride (5.1 g, 0.02 mol). K2CO3 (5.2 g, 0.04 mol), 1-[4-(4-bromobutoxy)-3-methoxyphenyl]ethanone (6.6 g, 22 mmol), and dimethylformamide (60 ml) was heated a 75° C. for 5 hours. The reaction was poured into water, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate was washed (water), dried (MgSO4), and the solvent was concentrated to yield initially an oil, which solidified upon standing. The solid was triturated with hexane and collected to afford 7.7 g of the product as a waxy solid. The compound was chromatographed on a Waters Prep 500 utilizing silica gel columns and eluting with dichloromethane/methanol (5%). Concentration of the appropriate fractions yielded 5.1 g of off-white solid 1-[4-[4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-butoxy]-3-methoxyphenyl]ethanone, which when recrystallized from ethyl alcohol yielded 3.2 g. (36%) of feathery white needles, m.p.=88°-90° C.

Fuente