반응 #2138867

반응 방정식

sodium hydride

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

3-(chloromethyl)-1-(phenylmethyl)pyrrolidine

→

1,3-dihydro-1-[1-(phenylmethyl)-3-pyrrolidinylmethyl]-2H-benzimidazol-2-one

수율 53.0%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGthe whole is stirred
2. 2
   온도The reaction mixture is cooled
3. 3
   workup.ADDITIONpoured onto water
4. 4
   추출The product is extracted with 4-methyl-2-pentanone
5. 5
   기타The extract is dried
6. 6
   여과filtered
7. 7
   기타evaporated
8. 8
   기타The residue is purified by column-chromatography over silica gel using
9. 9
   workup.ADDITIONa mixture of trichloromethane and methanol (95:5 by volume) as eluent
10. 10
    기타The pure fractions are collected
11. 11
    기타the eluent is evaporated
12. 12
    workup.STIRRINGthe whole is stirred for 1 hour at room temperature
13. 13
    온도After cooling
14. 14
    추출the product is extracted with 4-methyl-2-pentanone
15. 15
    기타The extract is dried
16. 16
    여과filtered
17. 17
    기타evaporated
18. 18
    기타The residue is triturated in 2,2'-oxybispropane with activated charcoal
19. 19
    여과The latter is filtered off
20. 20
    기타to crystallize
21. 21
    여과The product is filtered off
22. 22
    기타dried

실험 절차

To a stirred mixture of 43.5 parts of 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one and 270 parts of N,N-dimethylformamide are added portionwise 10 parts of sodium hydride dispersion 60%. After stirring for 1 hour at about 40°-50° C., there are added 53 parts of 3-(chloromethyl)-1-(phenylmethyl)pyrrolidine and the whole is stirred and heated overnight at about 110° C. The reaction mixture is cooled and poured onto water. The product is extracted with 4-methyl-2-pentanone. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is taken up in a diluted hydrochloric acid solution and the whole is stirred for 1 hour at room temperature. After cooling, the mixture is alkalized and the product is extracted with 4-methyl-2-pentanone. The extract is dried, filtered and evaporated. The residue is triturated in 2,2'-oxybispropane with activated charcoal. The latter is filtered off and the filtrate is allowed to crystallize. The product is filtered off and dried, yielding 40 parts (53%) of 1,3-dihydro-1-[1-(phenylmethyl)-3-pyrrolidinylmethyl]-2H-benzimidazol-2-one.

출처