Hydroxyamine hydrochloride → HCID 86694688, compound

HRID 475237Notes

Reaction equation

HRID 475237 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16](=O)[CH2:17][CH3:18])=[CH:15][C:10]=2[N:9]=[CH:8]1.Cl.[NH2:21][OH:22].CC([O-])=O.[Na+]>CO>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16](=[N:21][OH:22])[CH2:17][CH3:18])=[CH:15][C:10]=2[N:9]=[CH:8]1

Participants

5

Reactant 3

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

Product 1

HCID 86694688HCID 86694688, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 170 (100 mg, 0.39 mmol) in MeOH (5 mL) was added hydroxylamine hydrochloride (54 mg, 0.78 mmol) and NaOAc (100 mg, 1 mmol). The mixture was refluxed overnight. The mixture was extracted with EtOAc, washed sequentially with H2O and brine and dried (Na2SO4), filtered and concentrated in vacuo to afford 95 mg (90%) of 1-[1-(tetrahydro-pyran-2-yl)-1H-benzoimidazol-5-yl]-propan-1-one oxime (172) as a light yellow oil.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. extractionThe mixture was extracted with EtOAc
  3. washwashed sequentially with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-24c069b2aa984cc09f056025b4258c56
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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