反応 #2298669

反応方程式

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

K2CO3

1-[4-(3-bromopropoxy)-3-methoxyphenyl] phenylmethanone

→

off-white solid

収率 87.0%

1-[4-[3-[4-(6-Fluoro-1,2-Benzisoxazol-3-yl)-1- Piperidinyl]Propoxy]-3-Methoxyphenyl]Phenylmethanone

収率 87.0%

溶媒

acetonitrile

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度at reflux for 3 hours
3. 3
   その他At the end of reaction
4. 4
   濃縮the acetonitrile was concentrated
5. 5
   抽出the mixture was extracted into dichloromethane (200 ml)
6. 6
   ろ過The insolubles were filtered off
7. 7
   その他the solvent was evaporated to an oil
8. 8
   その他Purification
9. 9
   洗浄was carried out by flash chromatography over a silica gel column (SiO2, 50 g; eluted with dichloromethane, 600 ml; 1% methanol:dichloromethane. 600 ml; 2% methanol: 98% dichloromethane, 600 ml)
10. 10
    workup.ADDITIONThe fractions containing the pure product
11. 11
    濃縮concentrated

実験手順

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2- benzisoxazole (2.2 g, 10 mmoles), K2CO3 (2.3 g) and 1-[4-(3-bromopropoxy)-3-methoxyphenyl] phenylmethanone (3.47 g, 10 mmoles) in acetonitrile (100 ml) was heated at reflux for 3 hours. At the end of reaction, the acetonitrile was concentrated and the mixture was extracted into dichloromethane (200 ml). The insolubles were filtered off and the solvent was evaporated to an oil. Purification was carried out by flash chromatography over a silica gel column (SiO2, 50 g; eluted with dichloromethane, 600 ml; 1% methanol:dichloromethane. 600 ml; 2% methanol: 98% dichloromethane, 600 ml). The fractions containing the pure product were combined and concentrated to give 4.24 g (87%) of an off-white solid. Recrystallization from ethanol (75 ml) gave 3.9 g of 1-[4-[3-[4-(6-fluoro-1, 2-benziosoxazol-3-yl)-1-piperidinyl]propoxy]-3- methoxyphenyl]phenylmethanone as off-white crystals, m.p.=128°-30° C.

出典