반응 #83856

반응 방정식

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

K2CO3

1-[2-(3-bromopropoxy)-5-methylphenyl]ethanone

→

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

수율 46.2%

용매

dimethylformamide

acetonitrile

반응 조건

후처리

1. 1
   기타At the end of the reaction
2. 2
   농축the solvent was concentrated
3. 3
   추출the mixture was extracted into dichloromethane (300 ml)
4. 4
   세척The organic solution was washed with water and brine
5. 5
   건조dried over MgSO4
6. 6
   농축concentrated down to a crude oil
7. 7
   기타The purification
8. 8
   세척was done by flash chromatography over a silica gel column (SiO2, 60 g, eluted with 1% CH3OH:dichloromethane: 1.2 l; 3% CH3OH:dichloromethane: 600 ml)
9. 9
   기타The material thus obtained
10. 10
    기타was crystallized from a small volume of ether and hexane

실험 절차

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride (2.87 g, 11.23 mmol), K2CO3 (2.5 g), 1-[2-(3-bromopropoxy)-5-methylphenyl]ethanone (3.74 g, 13.8 mmol) in dimethylformamide (10 ml) and acetonitrile (.50 ml) was heated at 95° C. for 6 hours. At the end of the reaction, the solvent was concentrated and the mixture was extracted into dichloromethane (300 ml). The organic solution was washed with water and brine, dried over MgSO4, then concentrated down to a crude oil. The purification was done by flash chromatography over a silica gel column (SiO2, 60 g, eluted with 1% CH3OH:dichloromethane: 1.2 l; 3% CH3OH:dichloromethane: 600 ml). The material thus obtained was crystallized from a small volume of ether and hexane to provide 2.13 g (46%) of off-white 1-[2-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-5-methylphenyl]ethanone, m.p.=92°-93° C.

출처