반응 #83867

반응 방정식

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

K2CO3

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

→

off-white solid

수율 87.0%

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

수율 87.0%

용매

acetonitrile

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도at reflux for 3 hours
3. 3
   기타At the end of reaction
4. 4
   농축the acetonitrile was concentrated
5. 5
   추출the mixture was extracted into dichloromethane (200 ml)
6. 6
   여과The insolubles were filtered off
7. 7
   기타the solvent was evaporated to an oil
8. 8
   기타Purification
9. 9
   세척was 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
    농축concentrated

실험 절차

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.2 g, 10 mmol), K2CO3 (2.3 g) and 1-[4-(3-bromopropoxy)-3-methoxyphenyl]phenylmethanone (3.47 g, 10 mmol) 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-methoxyphenylmethanone as off-white crystals, m.p.=128°-130° C.

출처