Réaction #75161

Équation de réaction

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

1,3-dihydro-1-(1,2,3,6-tetrahydro-4-pyridinyl)-2H-benzimidazol-2-one

sodium carbonate

potassium iodide

→

1-{3-[3,6-dihydro-4-(1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)-1-(2H)-pyridinyl]propyl}-1,3-dihydro-2H-benzimidazol-2-one

Rendement 64.5%

Solvants

4-methyl-2-pentanone

water

Conditions de réaction

Traitement

1. 1
   Températurerefluxed for 48 hours
2. 2
   Autrethe layers are separated
3. 3
   AutreThe organic phase is dried
4. 4
   Filtrationfiltered
5. 5
   Autreevaporated
6. 6
   AutreThe residue is purified by column-chromatography over silica gel using
7. 7
   workup.ADDITIONa mixture of trichloromethane and 10% of methanol as eluent
8. 8
   AutreThe pure fractions are collected
9. 9
   Autrethe eluent is evaporated
10. 10
    AutreThe residue is crystallized from a mixture of N,N-dimethylformamide and water

Mode opératoire

A mixture of 2.3 parts of 1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one, 2.15 parts of 1,3-dihydro-1-(1,2,3,6-tetrahydro-4-pyridinyl)-2H-benzimidazol-2-one, 3.2 parts of sodium carbonate, 0.1 parts of potassium iodide and 80 parts of 4-methyl-2-pentanone is stirred and refluxed for 48 hours. After cooling to room temperature, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 10% of methanol 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, yielding 2.5 parts (64.5%) of 1-{3-[3,6-dihydro-4-(1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)-1-(2H)-pyridinyl]propyl}-1,3-dihydro-2H-benzimidazol-2-one; mp. 206.6° C.

Source