Reacción #75180

Ecuación de reacción

1-(3-chloropropyl)-1H-benzimidazole

1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one

sodium carbonate

potassium iodide

→

8-[3-(1H-benzimidazol-1-yl)propyl]-1-phenyl-1,3,8-triazaspiro-[4,5]decan-4-one

Rendimiento 25.0%

Disolventes

4-methyl-2-pentanone

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturarefluxed overnight
2. 2
   TemperaturaThe reaction mixture is cooled
3. 3
   Otrothe layers are separated
4. 4
   OtroThe organic phase is dried
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated
7. 7
   OtroThe residue is purified by column-chromatography over silica gel using
8. 8
   workup.ADDITIONa mixture of trichloromethane and methanol (90:10 by volume) as eluent
9. 9
   OtroThe pure fractions are collected
10. 10
    Otrothe eluent is evaporated
11. 11
    OtroThe residue is crystallized from 4-methyl-2-pentanone

Procedimiento

A mixture of 6 parts of 1-(3-chloropropyl)-1H-benzimidazole, 4.6 parts of 1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one, 10 parts of sodium carbonate, 0.1 parts of potassium iodide and 80 parts of 4-methyl-2-pentanone is stirred and refluxed overnight. The reaction mixture is cooled, 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 methanol (90:10 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 4-methyl-2-pentanone, yielding 2parts (25%) of 8-[3-(1H-benzimidazol-1-yl)propyl]-1-phenyl-1,3,8-triazaspiro-[4,5]decan-4-one; mp. 191° C.

Fuente