Benzyloxyamine hydrochloride → 1-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-one O-benzyl-oxime

HRID 451430Notes

Reaction equation

HRID 451430 reaction equation
[CH3:1][C:2]1[O:6][C:5]([N:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)=[N:4][N:3]=1.Cl.[CH2:15]([O:22][NH2:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])(=O)C.[NH4+]>CO>[CH2:15]([O:22][N:23]=[C:10]1[CH2:11][CH2:12][N:7]([C:5]2[O:6][C:2]([CH3:1])=[N:3][N:4]=2)[CH2:8][CH2:9]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 102312Benzyloxyamine hydrochlorideHCID 517165Ammonium AcetateHCID 583978531-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-one

Product 1

HCID 866567051-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-one O-benzyl-oximeYield 96.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(5-methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-one (1.52 g, 8.39 mmol), O-benzylhydroxylamine hydrochloride (1.50 g, 9.23 mmol) and ammonium acetate (1.62 g, 21.0 mmol) in MeOH (34.5 mL) was heated to reflux for 2 hours under nitrogen. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel using a gradient from AcOEt to AcOEt/EtOH 9:1 (v/v) as eluent to yield the title compound as a light yellow viscous oil (2.32 g, 96%).

Workup

  1. temperatureto reflux for 2 hours under nitrogen
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel using a gradient from AcOEt to AcOEt/EtOH 9:1 (v/v) as eluent

Sources & evidence

ORD record
ord-921f7c4c689b4915ae201a122a3a78fe
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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