Potassium Iodide → 4-(2,4-Difluorobenzoyl)-1-allylpiperidine oxime hydrochloride

HRID 370892Notes

Reaction equation

HRID 370892 reaction equation
[F:1][C:2]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:3]=1[C:4](=[N:11][OH:12])[CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[CH2:18](Br)[CH:19]=[CH2:20].[Cl-:22].[NH4+].[I-].[K+].[Cl-].[Na+]>CN(C)C=O.C(O)C.O>[ClH:22].[F:1][C:2]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:3]=1[C:4](=[N:11][OH:12])[CH:5]1[CH2:10][CH2:9][N:8]([CH2:20][CH:19]=[CH2:18])[CH2:7][CH2:6]1

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 5234Sodium Chloride2×HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 57352713(Z)-(2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime

Product 1

HCID 867386034-(2,4-Difluorobenzoyl)-1-allylpiperidine oxime hydrochlorideYield 43.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 4.80 g of 4-(2,4-difluorobenzoyl)piperidine oxime, 2.7 g of allyl bromide, 2.7 g of ammonium chloride and some crystals of potassium iodide in 50 ml of dimethylformamide was stirred under nitrogen at 85°-90° for 5 hrs. The reaction mixture was cooled, diluted with 30 ml of ethanol and added to 1000 ml of half saturated aqueous sodium chloride solution, prepared by diluting saturated sodium chloride solution with an equal volume of water. After 16 hrs, the solid was washed with water and dried. The solid was dissolved in 60 ml of ethanol and 1 ml of conc hydrochloric acid. After heating to 50°, the solvents were evaporated in vacuo. Recrystallization of the residue from isopropanol-ether gave 2.63 g (43.5%) of product, mp, 239°.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customprepared
  3. washthe solid was washed with water
  4. customdried
  5. dissolutionThe solid was dissolved in 60 ml of ethanol
  6. temperatureAfter heating to 50°
  7. customthe solvents were evaporated in vacuo
  8. customRecrystallization of the residue from isopropanol-ether

Sources & evidence

ORD record
ord-3ecd445b6c474bf18aa54e9c621cccbb
Source dataset
uspto-grants-1985_07
Patent number
US04528376

Reaction notes

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