Hydrochloric Acid → 1-Cyclohexyloxy-2,2,6,6-tetramethyl-piperidin-4-ol

HRID 133662

Reaction equation

HRID 133662 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]1([CH3:12])[CH3:11].Cl.OO.N=O.[CH2:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>O.O=[Fe].O=[Fe]O[Fe]=O.C(#N)C>[CH:18]1([O:1][N:2]2[C:7]([CH3:8])([CH3:9])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]2([CH3:12])[CH3:11])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

9

Reactant 5

HCID 313Hydrochloric Acid2×HCID 784Hydrogen PeroxideHCID 945NitroxylHCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 8078Cyclohexane

Product 1

HCID 113228111-Cyclohexyloxy-2,2,6,6-tetramethyl-piperidin-4-olYield 50%

Reagents, catalysts & solvents 3

HCID 16211978Iron oxide (Fe3O4)Catalyst2×HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Iron (II,III) oxide (0.107 g, 0.462 mmol) is added to a mixture of 2.51 g (14.6 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidin-4-ol, 24 ml of acetonitrile, and 15 ml of cyclohexane. The reaction mixture is brought to reflux, and a solution of 0.306 g of concentrated hydrochloric acid in 2 ml of water is added. A solution of 4.49 g (66 mmol) of 50% aqueous hydrogen peroxide is added dropwise over 70 minutes to the reaction mixture while the reaction temperature is maintained at 60-62 degrees. After approximately 65% of the peroxide is added, 0.055 g (0.238 mmol) of iron (II,III) oxide and a solution of 0.107 g of concentrated hydrochloric acid are added to the reaction mixture. The mixture is heated at reflux after the peroxide is added until GC analysis shows that the starting nitroxyl compound is no longer present. After work up and purification according to the procedure of Example 54, the yield of the title compound is 1.87 g (50% yield), GC assay 96%.

Workup

  1. temperatureto reflux
  2. temperatureis maintained at 60-62 degrees
  3. temperatureThe mixture is heated
  4. additionis added until GC analysis
  5. customAfter work up and purification

Sources & evidence

ORD record
ord-e2b408829ec848c1a03e4e5e7328dec1
Source dataset
uspto-grants-2008_06
Patent number
US07390904B2

Linked notes

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