反应 #75192

反应方程式

1-(4-chlorobutyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one

5-chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one

sodium carbonate

potassium iodide

→

5-chloro-1-{1-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)butyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one hemihydrate

收率 46.0%

溶剂

4-methyl-2-pentanone

water

反应条件

后处理

1. 1
   温度refluxed for 18 hours
2. 2
   温度After cooling
3. 3
   其他the layers are separated
4. 4
   其他The organic phase is dried
5. 5
   过滤filtered
6. 6
   其他evaporated
7. 7
   workup.DISSOLUTIONThe residue is dissolved in 40 parts of ethanol
8. 8
   workup.STIRRINGThe whole is stirred for 30 minutes
9. 9
   其他the solvent is evaporated
10. 10
    萃取The product is extracted with trichloromethane
11. 11
    其他The extract is dried
12. 12
    过滤filtered
13. 13
    其他evaporated
14. 14
    其他The residue is purified by column-chromatography over silica gel using
15. 15
    workup.ADDITIONa mixture of trichloromethane and methanol (90:10 by volume) as eluent
16. 16
    其他The pure fractions are collected
17. 17
    其他the eluent is evaporated
18. 18
    其他The residue is crystallized from a mixture of N,N-dimethylformamide and water
19. 19
    过滤The product is filtered off
20. 20
    其他dried

实验过程

A mixture of 9.25 parts of 1-(4-chlorobutyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one, 7.55 parts of 5-chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one, 10.6 parts of sodium carbonate, 0.1 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone is stirred and refluxed for 18 hours. After cooling, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is dissolved in 40 parts of ethanol and the solution is acidified with 30 parts of a concentrated hydrochloric acid solution. The whole is stirred for 30 minutes and the solvent is evaporated. The residue is suspended in water and the suspension is alkalized with ammonium hydroxide. The product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from a mixture of N,N-dimethylformamide and water. The product is filtered off and dried, yielding 6.5 parts (46%) of 5-chloro-1-{1-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)butyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one hemihydrate; mp. 258° C.

来源