Methyl Isobutyl Ketone → 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

HRID 46871Notes

Reaction equation

HRID 46871 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]1=[O:14].Cl.[CH3:16][N:17]1[C:21](=[O:22])[C:20]2([CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[N:19]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:18]1.C(=O)([O-])[O-].[Na+].[Na+].CC(C)CC(=O)C>O>[O:14]=[C:6]1[N:5]([CH2:4][CH2:3][CH2:2][N:25]2[CH2:26][CH2:27][C:20]3([N:19]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:18][N:17]([CH3:16])[C:21]3=[O:22])[CH2:23][CH2:24]2)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7]1

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 1977311,3,8-Triazaspiro(4.5)decan-4-one, 3-methyl-1-phenyl-, hydrochloride (1:1)HCID 18104191-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 203855678-[3-(1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl]-3-methyl-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-oneYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

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.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customthe layers are separated
  3. dry with materialThe 4-methyl-2-pentanone-phase is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by column-chromatography over silica gel using
  7. additiona mixture of trichloromethane and 5% of methanol as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated
  10. customThe residue is triturated in 4-methyl-2-pentanone
  11. filtrationThe solid product is filtered off
  12. customdried

Sources & evidence

ORD record
ord-469b644151a9415fbfd03bf85b206a76
Source dataset
uspto-grants-1979_11
Patent number
US04175129

Reaction notes

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