4-[1-(4-Bromo-2,5-difluoro-phenyl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid tert-butyl ester → 1-(4-bromo-2,5-difluoro-phenyl)-piperidin-4-one O-piperidin-4-yl-oxime

HRID 2066902Notes

Reaction equation

HRID 2066902 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][N:15]=[C:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[C:26]([F:28])[C:25]([Br:29])=[CH:24][C:23]=3[F:30])[CH2:18][CH2:17]2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH:8]1[CH2:13][CH2:12][CH:11]([O:14][N:15]=[C:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[C:26]([F:28])[C:25]([Br:29])=[CH:24][C:23]=3[F:30])[CH2:18][CH2:17]2)[CH2:10][CH2:9]1

Participants

3

Reactant 1

HCID 866550274-[1-(4-Bromo-2,5-difluoro-phenyl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866550281-(4-bromo-2,5-difluoro-phenyl)-piperidin-4-one O-piperidin-4-yl-oxime

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Compound 77a (300 mg, 0.61 mmol) was dissolved in 20% TFA/DCM (2 mL) and stirred at r.t. for 2 h. The solvents were removed in vacuo and the residue re-dissolved in DCM. This solution was washed with 2M NaOH then water and dried over MgSO4 and concentrated to give 1-(4-bromo-2,5-difluoro-phenyl)-piperidin-4-one O-piperidin-4-yl-oxime 77b.

Workup

  1. customThe solvents were removed in vacuo
  2. dissolutionthe residue re-dissolved in DCM
  3. washThis solution was washed with 2M NaOH
  4. dry with materialwater and dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8b380f8050a943f7a5ad28f61e7db843
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

Loading…