Potassium Iodide → 7-[4,4-bis(4-fluorophenyl)butyl]hexahydro-3,3-dimethylimidazo[1,5-a]pyrazin-1(5H)-one

HRID 35328Notes

Reaction equation

HRID 35328 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[CH3:20][C:21]1([CH3:31])[N:25]2[CH2:26][CH2:27][NH:28][CH2:29][CH:24]2[C:23](=[O:30])[NH:22]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH:5]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:4][CH2:3][CH2:2][N:28]2[CH2:27][CH2:26][N:25]3[C:21]([CH3:31])([CH3:20])[NH:22][C:23](=[O:30])[CH:24]3[CH2:29]2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 14230278hexahydro-3,3-dimethylimidazo(1,5-a)pyrazin-1(5H)-one

Product 1

HCID 142302807-[4,4-bis(4-fluorophenyl)butyl]hexahydro-3,3-dimethylimidazo[1,5-a]pyrazin-1(5H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 169.8 parts of 1,1'-(4-chlorobutylidene)bis[4-fluorobenzene], 93.5 parts of hexahydro-3,3-dimethylimidazo[1,5-a]pyrazin-1(5H)-one, 128.3 parts of sodium carbonate, 0.1 parts of potassium iodide and 1200 parts of 4-methyl-2-pentanone was stirred and refluxed for 8 hours using a water-separator. After cooling overnight to room temperature, the reaction mixture was filtered. The filtrate was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was triturated in 2,2'-oxybispropane. The product was filtered off and dried, yielding 108 parts of 7-[4,4-bis(4-fluorophenyl)butyl]hexahydro-3,3-dimethylimidazo[1,5-a]pyrazin-1(5H)-one; mp. 148.4° C. (intermediate 90).

Workup

  1. temperaturerefluxed for 8 hours
  2. temperatureAfter cooling overnight to room temperature
  3. filtrationthe reaction mixture was filtered
  4. customThe filtrate was evaporated
  5. customThe residue was purified by column-chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was triturated in 2,2'-oxybispropane
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-e6838801ccbd4ce59d0d38e7c8f17a03
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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