Water → HCID 86694688, compound

HRID 475088Notes

Reaction equation

HRID 475088 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[O:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[N:15]1[C:19]2[CH:20]=[CH:21][C:22]([C:24](=O)[CH2:25][CH3:26])=[CH:23][C:18]=2[N:17]=[CH:16]1.O>CO>[O:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[N:15]1[C:19]2[CH:20]=[CH:21][C:22]([C:24](=[N:2][OH:3])[CH2:25][CH3:26])=[CH:23][C:18]=2[N:17]=[CH:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 71272254HCID 71272254, compound

Product 1

HCID 86694688HCID 86694688, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydroxylamine hydrochloride (54 mg, 0.78 mmol) and sodium acetate (100 mg, 1 mmol) were added to a solution of 1-(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)propan-1-one (100 mg, 0.39 mmol) in MeOH (5 mL). The mixture was refluxed overnight. The mixture was poured into water and extracted with EtOAc. The organics were washed sequentially with water and brine, then (Na2SO4). Removal of solvent followed by SiO2 chromatography afforded 1-(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)propan-1-one oxime (95 mg, 90% yield) as a light yellow oil.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. extractionextracted with EtOAc
  3. washThe organics were washed sequentially with water and brine
  4. customRemoval of solvent

Sources & evidence

ORD record
ord-2cf9e9c9e50447ecbeada8799b3dcf02
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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