反応 #2271681

反応方程式

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

K2CO3

1-[4-(3-bromopropoxy)-3,5-dibromophenyl]ethanone

→

1-[3,5-dibromo-4-[3-[4-(6-fluoro-1,2- benzisoxazol-3-yl)-1-piperidinyl]propoxy]phenyl]ethanone

収率 58.7%

溶媒

acetonitrile

反応条件

後処理

1. 1
   温度at reflux for 3 hours
2. 2
   その他At the end of the reaction
3. 3
   その他the solvent was evaporated
4. 4
   抽出the residue wax extracted into dichloromethane (150 ml)
5. 5
   ろ過The insolubles were filtered off
6. 6
   濃縮-De dichloromethane solution was concentrated down to an oil
7. 7
   その他The purification
8. 8
   洗浄was done by flash chromatography on a silica gel column (SiO2, 47 g: eluted with dichloromethane, 300 ml; 1% methanol in dichloromethane, 600 ml)
9. 9
   その他The material thus purified as a colorless oil
10. 10
    その他Recrystallization from ethanol

実験手順

A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.0 g, 9.0 mmol). K2CO3 (1.3 g), and 1-[4-(3-bromopropoxy)-3,5-dibromophenyl]ethanone (2.65 g, 9.0 mmol) and acetonitrile (50 ml) was heated at reflux for 3 hours. At the end of the reaction, the solvent was evaporated and the residue wax extracted into dichloromethane (150 ml). The insolubles were filtered off. -De dichloromethane solution was concentrated down to an oil. The purification was done by flash chromatography on a silica gel column (SiO2, 47 g: eluted with dichloromethane, 300 ml; 1% methanol in dichloromethane, 600 ml). The material thus purified as a colorless oil, solidified on standing. Recrystallization from ethanol gave 1-[3,5-dibromo-4-[3-[4-(6-fluoro-1,2- benzisoxazol-3-yl)-1-piperidinyl]propoxy]phenyl]ethanone as white crystals (2.93 g, 57%), m.p.=102°-10 3° C.

出典