反応 #2271670

反応方程式

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

K2CO3

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

dimethylformamide

→

product

収率 87.4%

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

収率 87.4%

溶媒

water

反応条件

後処理

1. 1
   抽出the aqueous mixture was extracted with ethyl acetate
2. 2
   洗浄The ethyl acetate was washed (water)
3. 3
   乾燥dried (MgSO4)
4. 4
   濃縮the solvent was concentrated
5. 5
   その他to yield initially an oil, which
6. 6
   その他The solid was triturated with hexane
7. 7
   その他collected

実験手順

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.

出典