Ammonium Chloride → HCID 178482464, compound

HRID 1620587Notes

Reaction equation

HRID 1620587 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][CH2:10][CH:9]([CH:12]=O)[CH2:8][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(C)([O-])C.[K+].[Cl-].[NH4+]>C(O)C>[F:22][C:2]([F:23])([F:1])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:19])[F:20])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:7][CH2:8][CH:9](/[CH:12]=[C:29]2/[C:25]([NH:24][CH3:40])=[N:26][C:27](=[O:31])[N:28]/2[CH3:30])[CH2:10][CH2:11]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 178482464HCID 178482464, compoundYield 3.2%

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. 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 ethanol was evaporated under reduced pressure. Water and ethyl acetate were added to the residue, and the insoluble material was collected by filtration, recrystallized from ethanol/water, and further recrystallized from acetone/water. To a solution of the obtained solid (2.03 g) in toluene (10 mL) was added a solution (4.8 mL) of methylamine in 40% methanol at room temperature. The reaction mixture was stirred at 70° C. overnight, 40% methanol solution (4.8 mL) was added at room temperature, and the mixture was stirred at 70° C. overnight. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate) and recrystallized from ethyl acetate/heptane to give the title compound (1.10 g).

Workup

  1. temperaturecooling
  2. customethanol was evaporated under reduced pressure
  3. additionWater and ethyl acetate were added to the residue
  4. filtrationthe insoluble material was collected by filtration
  5. customrecrystallized from ethanol/water
  6. customfurther recrystallized from acetone/water
  7. additionTo a solution of the obtained solid (2.03 g) in toluene (10 mL) was added a solution (4.8 mL) of methylamine in 40% methanol at room temperature
  8. stirringThe reaction mixture was stirred at 70° C. overnight
  9. addition40% methanol solution (4.8 mL) was added at room temperature
  10. stirringthe mixture was stirred at 70° C. overnight
  11. customThe solvent was evaporated under reduced pressure
  12. customthe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate)
  13. customrecrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-125c7131868f4efa83bf432f063614a2
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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