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

HRID 1404317Notes

Reaction equation

HRID 1404317 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:7][CH:6]([OH:8])[CH2:5][C:4]([CH3:10])([CH3:9])[NH+:3]1[O-:11].OO.Cl.S(=O)(O)[O-].[Na+].[C:21](=O)([O-])O.[K+]>CC(C)=O.[Cu]Cl>[CH3:21][O:11][N:3]1[C:2]([CH3:12])([CH3:1])[CH2:7][CH:6]([OH:8])[CH2:5][C:4]1([CH3:10])[CH3:9]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 516893Potassium BicarbonateHCID 116079992,2,6,6-tetramethyl-4-hydroxypiperidine-N-oxideHCID 23665763Sodium Bisulfite

Product 1

HCID 109977701-Methoxy-2,2,6,6-tetramethyl-piperidin-4-ol

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 180AcetoneSolvent

Procedure

17.8 g (100 mmol) of 2,2,6,6-tetramethyl-4-hydroxypiperidine-N-oxide was dissolved in 100 ml of acetone, and 34 g (300 mmol) of 30% hydrogen peroxide aqueous solution was added slowly for more than 10 minutes. With a cooling to 5° C., 0.49 g (5.0 mol %) of copper (I) chloride was added with keeping the temperature of the reaction mixture in a range of 5° C. to 55° C. After 15 minutes, 0.5 g of 35% hydrochloric acid was added, and the reaction mixture was stirred at room temperature for 2 hours. After 2 hours, 50 ml of 4 mol/L sodium bisulfite aqueous solution, and 100 ml of saturated potassium hydrogen carbonate aqueous solution were added, and an extraction was carried out using 300 mL of ethyl acetate. The organic layer was concentrated by a rotary evaporator to obtain 1-methyloxy-2,2,6,6-tetramethyl-4-hydroxypiperidine.

Workup

  1. customin a range of 5° C. to 55° C
  2. waitAfter 2 hours
  3. extractionan extraction
  4. concentrationThe organic layer was concentrated by a rotary evaporator

Sources & evidence

ORD record
ord-3798bfb574e14106a8dec686391de927
Source dataset
uspto-grants-2014_12
Patent number
US08912287B2

Reaction notes

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