1-Phenyl-1,3,8-triazaspiro(4.5)decan-4-one → 8-[3-(5,6-dichloro-1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one

HRID 971756Notes

Reaction equation

HRID 971756 reaction equation
CS(O)(=O)=O.[Cl:6][C:7]1[C:20]([Cl:21])=[CH:19][C:10]2[N:11]([CH2:15][CH2:16][CH2:17]O)[C:12](=[O:14])[NH:13][C:9]=2[CH:8]=1.[C:22]1([N:28]2[C:32]3([CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[C:31](=[O:38])[NH:30][CH2:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[Cl:6][C:7]1[C:20]([Cl:21])=[CH:19][C:10]2[N:11]([CH2:15][CH2:16][CH2:17][N:35]3[CH2:34][CH2:33][C:32]4([N:28]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH2:29][NH:30][C:31]4=[O:38])[CH2:37][CH2:36]3)[C:12](=[O:14])[NH:13][C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 867353575,6-dichloro-1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one methanesulfonate

Product 1

HCID 203856358-[3-(5,6-dichloro-1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 8 parts of 5,6-dichloro-1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one methanesulfonate, 9.2 parts of 1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one and 90 parts of N,N-dimethylformamide is stirred and heated at 60° C. for one hour. The reaction mixture is evaporated and water is added to the residue. The whole is alkalized with ammonium hydroxide and 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 10% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The solid residue is triturated in 4-methyl-2-pentanone. The product is filtered off and dried, yielding 2 parts of 8-[3-(5,6-dichloro-1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one; mp. 275.2° C.

Workup

  1. customThe reaction mixture is evaporated
  2. additionwater is added to the residue
  3. extractionthe product is extracted with trichloromethane
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and 10% of methanol as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. customThe solid residue is triturated in 4-methyl-2-pentanone
  12. filtrationThe product is filtered off
  13. customdried

Sources & evidence

ORD record
ord-a4293401efbf480798d9cf064f79e97a
Source dataset
uspto-grants-1979_07
Patent number
US04160836

Reaction notes

Loading…