Reacción #75161

Ecuación de reacción

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

Rendimiento 64.5%

Disolventes

4-methyl-2-pentanone

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturarefluxed for 48 hours
2. 2
   Otrothe layers are separated
3. 3
   OtroThe organic phase is dried
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporated
6. 6
   OtroThe 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
   OtroThe pure fractions are collected
9. 9
   Otrothe eluent is evaporated
10. 10
    OtroThe residue is crystallized from a mixture of N,N-dimethylformamide and water

Procedimiento

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.

Fuente