反応 #75183

反応方程式

3-{3-[4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]propyl}-1,3-dihydro-5-methyl-1-(1-methylethenyl)-2H-benzimidazol-2-one

hydrochloric acid

ethanol

→

5-chloro-1-{1-[3-(2,3-dihydro-6-methyl-2-oxo-1H-benzimidazol-1-yl)-propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one hemihydrate

収率 40.0%

溶媒

water

反応条件

後処理

1. 1
   その他The reaction mixture is evaporated
2. 2
   workup.STIRRINGthe residue is stirred in ammonium hydroxide
3. 3
   抽出The product is extracted with trichloromethane
4. 4
   その他The extract is dried
5. 5
   ろ過filtered
6. 6
   その他evaporated
7. 7
   その他The residue is purified by column-chromatography over silica gel using
8. 8
   workup.ADDITIONa mixture of trichloromethane and methanol (95:5 by volume) as eluent
9. 9
   その他The pure fractions are collected
10. 10
    その他the eluent is evaporated
11. 11
    その他The residue is triturated in 4-methyl-2-pentanone
12. 12
    ろ過The product is filtered off
13. 13
    その他crystallized from a mixture of N,N-dimethylformamide and water

実験手順

A mixture of 6.4 parts of 3-{3-[4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]propyl}-1,3-dihydro-5-methyl-1-(1-methylethenyl)-2H-benzimidazol-2-one, 24 parts of a concentrated hydrochloric acid solution, 80 parts of ethanol and 50 parts of water is stirred for 1 hour at room temperature. The reaction mixture is evaporated and the residue is stirred in ammonium hydroxide. The product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is triturated in 4-methyl-2-pentanone. The product is filtered off and crystallized from a mixture of N,N-dimethylformamide and water, yielding 2.5 parts (40%) of 5-chloro-1-{1-[3-(2,3-dihydro-6-methyl-2-oxo-1H-benzimidazol-1-yl)-propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one hemihydrate; mp. 195.4° C.

出典