반응 #83853

반응 방정식

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

K2CO3

1-[3-(3-chloropropoxy)-4-methoxy-phenyl]phenylmethanone

→

1-[3-[3-[4-(6- fluoro-1,2-benzisoxa zol-3-yl)-1-piperidinyl]propoxy]-4-methoxyphenyl]-phenylmethanone

용매

acetonitrile

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도at reflux for 4 hours
3. 3
   기타At the end of the reaction
4. 4
   기타the solvent was evaporated
5. 5
   기타the residue was partitioned between water (150 ml) and dichloromethane (400 ml)
6. 6
   세척The dichloromethane solution was washed with water and brine (100 ml)
7. 7
   건조dried over MgSO4
8. 8
   농축concentrated to an oil
9. 9
   기타The purification
10. 10
    세척was done by flash chromatography over a silica gel column (SiO2, 40 g; eluted with dichloromethane, 300 ml; 1% methanol in dichloromethane, 850 ml)
11. 11
    기타The material thus obtained as a colorless oil
12. 12
    기타Recrystallization from ethanol (150 ml)

실험 절차

A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2 benzisoxazole (2.01 g; 9.13 mmol), K2CO3 (2.0 g), and 1-[3-(3-chloropropoxy)-4-methoxy-phenyl]phenylmethanone (3.93 g; 11.3 mmol) and acetonitrile (50 ml) was heated at reflux for 4 hours. At the end of the reaction, the solvent was evaporated and the residue was partitioned between water (150 ml) and dichloromethane (400 ml). The dichloromethane solution was washed with water and brine (100 ml), dried over MgSO4, then concentrated to an oil. The purification was done by flash chromatography over a silica gel column (SiO2, 40 g; eluted with dichloromethane, 300 ml; 1% methanol in dichloromethane, 850 ml). The material thus obtained as a colorless oil solidified on standing. Recrystallization from ethanol (150 ml) gave 1-[3-[3-[4-(6- fluoro-1,2-benzisoxa zol-3-yl)-1-piperidinyl]propoxy]-4-methoxyphenyl]-phenylmethanone as white crystals, 3.07 g (63%), m.p.=140°-141° C.

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