Reaktion #75161

Reaktionsgleichung

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

Ausbeute 64.5%

Lösungsmittel

4-methyl-2-pentanone

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed for 48 hours
2. 2
   Sonstigethe layers are separated
3. 3
   SonstigeThe organic phase is dried
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe 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
   SonstigeThe pure fractions are collected
9. 9
   Sonstigethe eluent is evaporated
10. 10
    SonstigeThe residue is crystallized from a mixture of N,N-dimethylformamide and water

Vorschrift

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.

Quelle