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

HRID 1459963Notes

Reaction equation

HRID 1459963 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-966da81f3cf547ee97193a1f43b8bf85
Source dataset
uspto-grants-1998_12
Patent number
US05854263

Reaction notes

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