반응 #75193

반응 방정식

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

1-(1-methylethyl)-3-(4-piperidinyl)-2H-benzimidazol-2-one

sodium carbonate

potassium iodide

→

1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-3-(1-methylethyl)-2H-benzimidazol-2-one

수율 64.0%

용매

4-methyl-2-pentanone

water

반응 조건

후처리

1. 1
   온도refluxed overnight
2. 2
   기타the layers are separated
3. 3
   기타The organic phase is dried
4. 4
   여과filtered
5. 5
   기타evaporated
6. 6
   workup.STIRRINGThe residue is stirred for 30 minutes with a solution of 12 parts of a concentrated hydrochloric acid solution in 40 parts of ethanol
7. 7
   기타The solvent is evaporated
8. 8
   추출the product is extracted with trichloromethane
9. 9
   기타The extract is dried
10. 10
    여과filtered
11. 11
    기타evaporated
12. 12
    기타The residue is purified by column-chromatography over silica gel using
13. 13
    workup.ADDITIONa mixture of trichloromethane and methanol (95:5 by volume) as eluent
14. 14
    기타The pure fractions are collected
15. 15
    기타the eluent is evaporated
16. 16
    기타The residue is crystallized from 4-methyl-2-pentanone
17. 17
    여과The product is filtered off
18. 18
    기타dried

실험 절차

A mixture of 4.15 parts of 1-(3-chloropropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one, 3.9 parts of 1-(1-methylethyl)-3-(4-piperidinyl)-2H-benzimidazol-2-one, 3.2 parts of sodium carbonate, 0.1 parts of potassium iodide and 120 parts of 4-methyl-2-pentanone is stirred and refluxed overnight. The reaction mixture is cooled to room temperature, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is stirred for 30 minutes with a solution of 12 parts of a concentrated hydrochloric acid solution in 40 parts of ethanol. The solvent is evaporated and the residue is suspended in water. The suspension is alkalized with a diluted ammonium hydroxide solution and 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 (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 4-methyl-2-pentanone. The product is filtered off and dried, yielding 4.2 parts (64%) of 1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-3-(1-methylethyl)-2H-benzimidazol-2-one; mp. 174.3° C.

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