Hydroxyamine hydrochloride → (2,4-Difluorophenyl)[1-(phenylmethyl)-3-pyrrolidinyl]methanone oxime

HRID 567498Notes

Reaction equation

HRID 567498 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH:11]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12]1)=O.[NH2:23][OH:24].Cl.C([O-])(=O)C.[NH4+]>C(O)C.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH:11]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12]1)=[N:23][OH:24]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517165Ammonium AcetateHCID 21960053(2,4-Difluorophenyl)[1-(phenylmethyl)-3-pyrrolidinyl]methanone

Product 1

HCID 73856697(2,4-Difluorophenyl)[1-(phenylmethyl)-3-pyrrolidinyl]methanone oximeYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To the compound (2,4-difluorophenyl)[1-(phenylmethyl)-3-pyrrolidinyl]methanone (22 g) in 95% ethanol (350 ml) and water (100 ml) was added NH2OH.HCl (10.1 g) and ammonium acetate (12.7 g, 2.1 eq). The resulting mixture was refluxed for 3.5 hours. The mixture was then allowed to stir at room temperature for 24 hours. The reaction mixture was concentrated to remove ethanol, poured into water (500 ml), and extracted with dichloromethane (500 ml). This was followed by washing with water, brine, and drying over magnesium sulfate. The product was concentrated to an oil and purified by column chromatography to yield 12 g of (2,4-difluorophenyl)[1-(phenylmethyl)-3-pyrrolidinyl]methanone oxime.

Workup

  1. temperatureThe resulting mixture was refluxed for 3.5 hours
  2. concentrationThe reaction mixture was concentrated
  3. customto remove ethanol
  4. additionpoured into water (500 ml)
  5. extractionextracted with dichloromethane (500 ml)
  6. washby washing with water, brine
  7. dry with materialdrying over magnesium sulfate
  8. concentrationThe product was concentrated to an oil
  9. custompurified by column chromatography

Sources & evidence

ORD record
ord-9ac11ef66bb64e3d96447563f6f152e0
Source dataset
uspto-grants-2001_01
Patent number
USRE037029E1

Reaction notes

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