1-Phenyl-5-(3-propylphenyl)-4,5-dihydro-1H-pyrazol-3-ylamine → 1-Phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamine

HRID 83515Notes

Reaction equation

HRID 83515 reaction equation
[C:1]1([N:7]2[CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][CH3:20])[CH:13]=3)[CH2:10][C:9]([NH2:21])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1(C)C=CC=CC=1>[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][CH3:20])[CH:13]=3)=[CH:10][C:9]([NH2:21])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 712877421-Phenyl-5-(3-propylphenyl)-4,5-dihydro-1H-pyrazol-3-ylamine

Product 1

HCID 712877391-Phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamineYield 47%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the crude product of 1-phenyl-5-(3-propylphenyl)-4,5-dihydro-1H-pyrazol-3-ylamine (18.6 g) in toluene (185 ml) was added activated carbon (pH5 to 8, 9.29 g), and the mixture was stirred overnight under oxygen atmosphere at reflux. This reaction solution was cooled to room temperature, and then the activated carbon was filtered off through Celite, and eluted with ethyl acetate. This filtrate was concentrated under reduced pressure, the resulting residue was dissolved in toluene (185 ml), and to the solution was added fresh activated carbon (pH5 to 8, 9.29 g), and the mixture was stirred overnight under oxygen atmosphere at reflux. This reaction solution was cooled to room temperature, and then the activated carbon was filtered off through Celite, and eluted with ethyl acetate. This filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1 to 1/1) to give the titled compound (8.68 g).

Workup

  1. temperatureat reflux
  2. filtrationthe activated carbon was filtered off through Celite
  3. washeluted with ethyl acetate
  4. concentrationThis filtrate was concentrated under reduced pressure
  5. dissolutionthe resulting residue was dissolved in toluene (185 ml)
  6. additionto the solution was added fresh activated carbon (pH5 to 8, 9.29 g)
  7. stirringthe mixture was stirred overnight under oxygen atmosphere
  8. temperatureat reflux
  9. temperatureThis reaction solution was cooled to room temperature
  10. filtrationthe activated carbon was filtered off through Celite
  11. washeluted with ethyl acetate
  12. concentrationThis filtrate was concentrated under reduced pressure
  13. customthe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1 to 1/1)

Sources & evidence

ORD record
ord-dddac6624c50444c99b32e387ba30678
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

Loading…