Hydroxyamine hydrochloride → 1-Methyl-4-(2-fluorobenzoyl)piperidine oxime

HRID 370891Notes

Reaction equation

HRID 370891 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8](=O)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[CH2:4][CH2:3]1.Cl.[NH2:18][OH:19].C([O-])(=O)C.[NH4+]>C(O)C.O>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8](=[N:18][OH:19])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517165Ammonium AcetateHCID 131803174-(2-Fluorobenzoyl)-1-methylpiperidine

Product 1

HCID 867390501-Methyl-4-(2-fluorobenzoyl)piperidine oximeYield 54%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 5.2 g of 1-methyl-4-(2-fluorobenzoyl)piperidine, 2.5 g of hydroxylamine hydrochloride, 5.4 g of ammonium acetate and 50+15 ml of ethanol-water was heated under reflux for 22 hrs. Most of the ethanol was removed under reduced pressure. The aqueous mixture was made basic with aqueous sodium hydroxide and the mixture was extracted with chloroform. The chloroform extract was dried over anhydrous magnesium sulfate and the chloroform was evaporated in vacuo to give a solid. The solid was triturated with ether. Recrystallization from ethanol-water gave 3.0 g (52.6%) of product, mp, 136°-139°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 22 hrs
  3. customMost of the ethanol was removed under reduced pressure
  4. extractionthe mixture was extracted with chloroform
  5. extractionThe chloroform extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customthe chloroform was evaporated in vacuo
  8. customto give a solid
  9. customThe solid was triturated with ether
  10. customRecrystallization from ethanol-water

Sources & evidence

ORD record
ord-f515a508638f4d3dba038d209b6482db
Source dataset
uspto-grants-1985_07
Patent number
US04528376

Reaction notes

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