Potassium Iodide → 5-chloro-1-{1-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)butyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one hemihydrate

HRID 1704602

반응식

HRID 1704602 반응식
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8](C(C)=C)[C:7]1=[O:18].[Cl:19][C:20]1[CH:35]=[CH:34][C:23]2[N:24]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[C:25](=[O:27])[NH:26][C:22]=2[CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[OH2:18].[Cl:19][C:20]1[CH:35]=[CH:34][C:23]2[N:24]([CH:28]3[CH2:29][CH2:30][N:31]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]4[C:10]5[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=5[NH:8][C:7]4=[O:18])[CH2:32][CH2:33]3)[C:25](=[O:27])[NH:26][C:22]=2[CH:21]=1.[Cl:19][C:20]1[CH:35]=[CH:34][C:23]2[N:24]([CH:28]3[CH2:29][CH2:30][N:31]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]4[C:10]5[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=5[NH:8][C:7]4=[O:18])[CH2:32][CH2:33]3)[C:25](=[O:27])[NH:26][C:22]=2[CH:21]=1

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 130168791-(4-chlorobutyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one

생성물 1

HCID 706010085-chloro-1-{1-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)butyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one hemihydrate수율 46%

시약·촉매·용매 2

HCID 962Water용매HCID 7909Methyl Isobutyl Ketone용매

실험 절차

A mixture of 9.25 parts of 1-(4-chlorobutyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one, 7.55 parts of 5-chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one, 10.6 parts of sodium carbonate, 0.1 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone is stirred and refluxed for 18 hours. After cooling, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is dissolved in 40 parts of ethanol and the solution is acidified with 30 parts of a concentrated hydrochloric acid solution. The whole is stirred for 30 minutes and the solvent is evaporated. The residue is suspended in water and the suspension is alkalized with 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 (90:10 by volume) 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. The product is filtered off and dried, yielding 6.5 parts (46%) of 5-chloro-1-{1-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)butyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one hemihydrate; mp. 258° C.

후처리

  1. temperaturerefluxed for 18 hours
  2. temperatureAfter cooling
  3. customthe layers are separated
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe residue is dissolved in 40 parts of ethanol
  8. stirringThe whole is stirred for 30 minutes
  9. customthe solvent is evaporated
  10. extractionThe product is extracted with trichloromethane
  11. customThe extract is dried
  12. filtrationfiltered
  13. customevaporated
  14. customThe residue is purified by column-chromatography over silica gel using
  15. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  16. customThe pure fractions are collected
  17. customthe eluent is evaporated
  18. customThe residue is crystallized from a mixture of N,N-dimethylformamide and water
  19. filtrationThe product is filtered off
  20. customdried

출처 및 근거

ORD 기록
ord-46883f3a238f4fc99cd88e7c4f2dfdec
출처 데이터셋
uspto-grants-1978_11
특허 번호
US04126688

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