Pyridine → 4-Dimethylaminocyclohexanone 4-bromophenylhydrazone

HRID 726332Notes

Reaction equation

HRID 726332 reaction equation
[CH3:1][N:2]([CH3:10])[CH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.Cl.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][NH2:20])=[CH:15][CH:14]=1.N1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][N:20]=[C:6]2[CH2:7][CH2:8][CH:3]([N:2]([CH3:10])[CH3:1])[CH2:4][CH2:5]2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 121574-Bromophenylhydrazine hydrochlorideHCID 103745454-(Dimethylamino)cyclohexan-1-one

Product 1

HCID 226114894-Dimethylaminocyclohexanone 4-bromophenylhydrazoneYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 6.0 gm (42.0 mMol) 4-dimethylaminocyclohexanone and 9.5 gm (42.0 mMol) 4-bromophenylhydrazine hydrochloride in 100 mL ethanol were added 3.4 mL (42 mMol) pyridine. The resultant mixture was then heated at reflux for 2 hours and then stirred at ambient temperature for 18 hours. The reaction mixture was then treated with aqueous potassium carbonate and extracted well with dichloromethane. The organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. The resultant residue was treated with toluene and concentrated again under reduced pressure to give 11.3 gm (87%) of the desired compound.

Workup

  1. temperatureat reflux for 2 hours
  2. extractionextracted well with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionThe resultant residue was treated with toluene
  6. concentrationconcentrated again under reduced pressure

Sources & evidence

ORD record
ord-761fa6a935da4198888316d4862f2564
Source dataset
uspto-grants-1998_01
Patent number
US05708187

Reaction notes

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