Reaktion #75149

Reaktionsgleichung

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

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

sodium carbonate

4-methyl-2-pentanone

→

8-[3-(1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl]-3-methyl-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one

Ausbeute 50.0%

Lösungsmittel

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture is cooled
2. 2
   Sonstigethe layers are separated
3. 3
   TrocknenThe 4-methyl-2-pentanone-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 5% of methanol as eluent
8. 8
   SonstigeThe pure fractions are collected
9. 9
   Sonstigethe eluent is evaporated
10. 10
    SonstigeThe residue is triturated in 4-methyl-2-pentanone
11. 11
    FiltrationThe solid product is filtered off
12. 12
    Sonstigedried

Vorschrift

A mixture of 4.8 parts of 1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one, 5.6 parts of 3-methyl-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one hydrochloride, 7.4 parts of sodium carbonate and 200 parts of 4-methyl-2-pentanone is stirred and refluxed overnight with water-separator. The reaction mixture is cooled, water is added and the layers are separated. The 4-methyl-2-pentanone-phase is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The residue is triturated in 4-methyl-2-pentanone. The solid product is filtered off and dried, yielding 4.0 parts (50%) of 8-[3-(1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl]-3-methyl-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one; mp. 186° C.

Quelle