Dimethylformamide → 3-[4-[4-(4-Methoxyphenyl)-1-piperazinyl]phenyl]-5,5-dimethyl-1-(1-methyl-2-oxopropyl)-2,4-imidazolidinedione

HRID 414244

Reaction equation

HRID 414244 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[C:25](=[O:26])[C:24]([CH3:28])([CH3:27])[NH:23][C:22]4=[O:29])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Cl[CH:31]([CH3:35])[C:32](=[O:34])[CH3:33].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:16]=[CH:17][C:18]([N:21]4[C:25](=[O:26])[C:24]([CH3:27])([CH3:28])[N:23]([CH:31]([CH3:35])[C:32](=[O:34])[CH3:33])[C:22]4=[O:29])=[CH:19][CH:20]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 200263-Chloro-2-butanoneHCID 21281918HCID 21281918, compound

Product 1

HCID 212819093-[4-[4-(4-Methoxyphenyl)-1-piperazinyl]phenyl]-5,5-dimethyl-1-(1-methyl-2-oxopropyl)-2,4-imidazolidinedioneYield 30.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 21.3 parts of 3-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-5,5-dimethyl-2,4-imidazolidinedione, 7.5 parts of 3-chloro-2-butanone, 6.0 parts of potassium carbonate and 180 parts of N,N-dimethylformamide was stirred overnight at 100° C. After cooling, the reaction mixture was diluted with 700 parts of water. The crystallized product was filtered off and purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98.5:1.5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. After trituration of the residue in methanol, the product was filtered off and crystallized from 4-methyl-2-pentanone, yielding 7.77 parts (30.9%) of 3-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-5,5-dimethyl-1-(1-methyl-2-oxopropyl)-2,4-imidazolidinedione; mp. 225.9° C. (intermediate 20).

Workup

  1. temperatureAfter cooling
  2. filtrationThe crystallized product was filtered off
  3. custompurified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (98.5:1.5 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. filtrationAfter trituration of the residue in methanol, the product was filtered off
  8. customcrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-cda9f5f992754127aeec712b73c700ee
Source dataset
uspto-grants-1988_12
Patent number
US04791111

Linked notes

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