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

HRID 223566Notes

Reaction equation

HRID 223566 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 138° 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 138° 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-b2f5278564fa4695a3d5ef982d19ff29
Source dataset
uspto-grants-1982_10
Patent number
US04355037

Reaction notes

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