Ethanol → 4-[(2,4-Dichlorophenyl)(hydroxyimino)methyl]-1-piperidinecarboxaldehyde

HRID 2417709Notes

Reaction equation

HRID 2417709 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH:12]=[O:13])[CH2:8][CH2:7]1)=O.Cl.[NH2:20][OH:21].C([O-])(=O)C.[NH4+].C(O)C>O>[CH:12]([N:9]1[CH2:10][CH2:11][CH:6]([C:4](=[N:20][OH:21])[C:3]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:2]=2[Cl:1])[CH2:7][CH2:8]1)=[O:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 517165Ammonium AcetateHCID 134508954-(2,4-Dichlorobenzoyl)piperidine-1-carbaldehyde

Product 1

HCID 886431994-[(2,4-Dichlorophenyl)(hydroxyimino)methyl]-1-piperidinecarboxaldehydeYield 14.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 105 g of 4-(2,4-dichlorobenzoyl)-1-formylpiperidine, 70 g of hydroxylamine hydrochloride, 135.0 g of ammonium acetate, 1.05 l of ethanol and 350 ml of water was stirred and heated at 130° for 40 hrs. The reaction mixture was evaporated and 2 l of water was added to the residue. The water was decanted from the oil and oil was washed two times with 500 ml water and then dissolved in about 400 ml dichloromethane. The insoluble material was collected. The dichloromethane extract was washed twice with 600 ml of water and the organic extract was evaporated. Trituration with diisopropyl ether and crystallization from acetone/ether gave 15.6 g (14.2%) of product, mp, 149°-150°.

Workup

  1. temperatureheated at 130° for 40 hrs
  2. customThe reaction mixture was evaporated
  3. addition2 l of water was added to the residue
  4. customThe water was decanted from the oil and oil
  5. washwas washed two times with 500 ml water
  6. dissolutiondissolved in about 400 ml dichloromethane
  7. customThe insoluble material was collected
  8. extractionThe dichloromethane extract
  9. washwas washed twice with 600 ml of water
  10. extractionthe organic extract
  11. customwas evaporated
  12. customTrituration with diisopropyl ether and crystallization from acetone/ether

Sources & evidence

ORD record
ord-a6cf46e312f9492b916b02016587ee88
Source dataset
uspto-grants-1984_09
Patent number
US04469869

Reaction notes

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