Ethanol → 1-Acetyl-4-(2,4-dichlorobenzoyl)piperidine oxime

HRID 370888Notes

Reaction equation

HRID 370888 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:14])[CH3:13])[CH2:8][CH2:7]1)=O.Cl.[NH2:21][OH:22].C([O-])(=O)C.[NH4+].C(O)C>O>[C:12]([N:9]1[CH2:10][CH2:11][CH:6]([C:4](=[N:21][OH:22])[C:3]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:2]=2[Cl:1])[CH2:7][CH2:8]1)(=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 517165Ammonium AcetateHCID 130763874-(2,4-dichlorobenzoyl)-N-acetylpiperidine

Product 1

HCID 860278721-Acetyl-4-(2,4-dichlorobenzoyl)piperidine oximeYield 31.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 13.0 g of 4-(2,4-dichlorobenzoyl)-N-acetylpiperidine, 6.8 g of hydroxylamine hydrochloride, 13.5 g of ammonium acetate, 127 ml of ethanol and 43 ml of water was stirred and heated at 130° for 24 hrs. The reaction mixture was evaporated and 1.3 l of water was added to the residue. The water was decanted from the oil and the oil was dissolved in about 150 ml dichloromethane. After washing with about 150 ml of water, drying over anhydrous magnesium sulfate and evaporating the solvent, an oil was obtained, which after crystallization from methanol/ether gave 4.25 g (31.1%) of product, mp, 167°-168°.

Workup

  1. temperatureheated at 130° for 24 hrs
  2. customThe reaction mixture was evaporated
  3. addition1.3 l of water was added to the residue
  4. customThe water was decanted from the oil
  5. dissolutionthe oil was dissolved in about 150 ml dichloromethane
  6. washAfter washing with about 150 ml of water
  7. dry with materialdrying over anhydrous magnesium sulfate
  8. customevaporating the solvent
  9. customan oil was obtained
  10. customwhich after crystallization from methanol/ether

Sources & evidence

ORD record
ord-98c6a174e4ec4b768356c87ae65a7c37
Source dataset
uspto-grants-1985_07
Patent number
US04528376

Reaction notes

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