Ammonium Chloride → HCID 86678755, compound

HRID 1620580Notes

Reaction equation

HRID 1620580 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11]CC(C=O)C[CH2:7]1.[NH:24]=[C:25]1[CH2:29][N:28]([CH3:30])[C:27](=[O:31])[N:26]1C(C1C=CC=CC=1)=O.[CH3:40][C:41]([CH3:44])([O-])[CH3:42].[K+].[Cl-].[NH4+]>C(O)C>[NH2:24][C:25]1=[N:26][C:27](=[O:31])[N:28]([CH3:30])/[C:29]/1=[CH:40]/[CH:41]1[CH2:44][CH2:11][N:6]([CH2:5][C:4]2[CH:14]=[CH:15][C:16]([C:18]([F:20])([F:19])[F:21])=[CH:17][C:3]=2[C:2]([F:23])([F:22])[F:1])[CH2:7][CH2:42]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 67504117HCID 67504117, compoundHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde

Product 1

HCID 86678755HCID 86678755, compoundYield 0.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (26.0 g) in ethanol (100 mL) were added 4-imino-1-methyl-3-(phenylcarbonyl)imidazolidin-2-one (16.7 g) and potassium tert-butoxide (8.60 g) under ice-cooling, and the reaction mixture was stirred at 80° C. for 2 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution at room temperature, and the solvent was evaporated under reduced pressure. Water and ethyl acetate were added to the residue, and the insoluble material was removed by filtration. The filtrate was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate under reduced pressure, and the solvent was evaporated. The residue was purified by silica gel column chromatography (ethyl acetate/methanol) and recrystallized from ethanol/water to give the title compound (220 mg).

Workup

  1. temperaturecooling
  2. customthe solvent was evaporated under reduced pressure
  3. additionWater and ethyl acetate were added to the residue
  4. customthe insoluble material was removed by filtration
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate under reduced pressure
  8. customthe solvent was evaporated
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)
  10. customrecrystallized from ethanol/water

Sources & evidence

ORD record
ord-069d9692cc37498390aca6bd7cdbd739
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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