反応 #2298664

反応方程式

3-(1-piperazinyl)-1,2-benzisothiazole

1-[4-(4-bromobutoxy)-3-methoxyphenyl]ethanone

K2CO3

→

1-[4-[4-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]butoxy]-3-methoxyphenyl]ethanone

収率 39.0%

溶媒

acetonitrile

反応条件

後処理

1. 1
   温度at reflux under N2 for 5 hours
2. 2
   その他Most of the solvent was removed in vacuo
3. 3
   その他the resultant gummy residue was partitioned between ethyl acetate and water
4. 4
   抽出The organic extract
5. 5
   洗浄was washed with water
6. 6
   乾燥dried with MgSO4
7. 7
   濃縮concentrated
8. 8
   その他to yield 7.8 g
9. 9
   その他Purification by preparative HPLC (Waters Associates Prep LC/System 500, utilizing 2 silica gel columns and 4% methanol-methylene chloride as eluent)
10. 10
    その他afforded 6.5 g of a damp, off-white solid
11. 11
    その他The product was recrystallized twice from toluene

実験手順

A mixture of 3-(1-piperazinyl)-1,2-benzisothiazole (4.0 g, 0.0182 mol), 1-[4-(4-bromobutoxy)-3-methoxyphenyl]ethanone (6.0 g, 0.0200 mol), K2CO3 (3.0 g, 0.0218 mol), KI (200 mg), and acetonitrile (125 ml) was stirred at reflux under N2 for 5 hours. Most of the solvent was removed in vacuo and the resultant gummy residue was partitioned between ethyl acetate and water. The organic extract was washed with water, dried with MgSO4, and concentrated to yield 7.8 g. Purification by preparative HPLC (Waters Associates Prep LC/System 500, utilizing 2 silica gel columns and 4% methanol-methylene chloride as eluent) afforded 6.5 g of a damp, off-white solid. The product was recrystallized twice from toluene to provide 3.1 g (39%) of 1-[4-[4-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]butoxy]-3-methoxyphenyl]ethanone as a white solid, m.p.=114°-116° C.

出典