Hydrochloric Acid → HCID 22902713, compound

HRID 741781Notes

Reaction equation

HRID 741781 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:7][C:6](=[N:8][OH:9])[CH2:5][C:4]([CH3:11])([CH3:10])[NH:3]1.Cl.[H][H].Cl.NO.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CO.O.[Pt].[Pt]=O.CN(C)C=O>[CH2:19]([N:8]([CH:6]1[CH2:5][C:4]([CH3:11])([CH3:10])[NH:3][C:2]([CH3:12])([CH3:1])[CH2:7]1)[OH:9])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

12

Reactant 6

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 778324-Piperidinone, 2,2,6,6-tetramethyl-, oximeHCID 443297Hydroxyamine hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 22902713HCID 22902713, compoundYield 67.2%

Reagents, catalysts & solvents 5

HCID 23939PlatinumCatalystHCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,2,6,6-tetramethylpiperidin-4-one oxime (15.0 g, 88 mmol), 40 ml of 5 N hydrochloric acid in methanol, 120 ml of methanol and 40 ml of water is subjected to 3 atmospheres of hydrogen over platinum oxide and 5% platinum on carbon for 18 hours. The reaction mixture is filtered through celite and concentrated. The crude hydroxylamine hydrochloride is added to 130 ml of N,N-dimethylformamide along with benzyl bromide (13.7 g, 80 mmol) and potassium carbonate (33.0 g, 240 mmol). The mixture is stirred for 16 hours. The mixture is then filtered and concentrated. The residue is partitioned between methylene chloride and dilute aqueous sodium carbonate. The organic layer is washed with water and brine, dried over anhydrous sodium sulfate and then concentrated to give 14.1 g of a white solid. This solid is recrystallized from ethanol to yield 6.8 g of the title compound in a 30% overall yield. The compound melts at 154° C.

Workup

  1. filtrationThe reaction mixture is filtered through celite
  2. concentrationconcentrated
  3. filtrationThe mixture is then filtered
  4. concentrationconcentrated
  5. customThe residue is partitioned between methylene chloride and dilute aqueous sodium carbonate
  6. washThe organic layer is washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ade86b049c03405cb0c7e445acca7899
Source dataset
uspto-grants-1996_09
Patent number
US05552464

Reaction notes

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