Acetic Anhydride → 4-acetyloxy-2,2,6,6-tetramethylpiperidine-N-oxide

HRID 1404314Notes

Reaction equation

HRID 1404314 reaction equation
C(N(CC)CC)C.[OH:8][CH:9]1[CH2:14][C:13]([CH3:16])([CH3:15])[NH+:12]([O-:17])[C:11]([CH3:19])([CH3:18])[CH2:10]1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>O1CCCC1>[C:20]([O:8][CH:9]1[CH2:14][C:13]([CH3:15])([CH3:16])[NH+:12]([O-:17])[C:11]([CH3:19])([CH3:18])[CH2:10]1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 116079992,2,6,6-tetramethyl-4-hydroxypiperidine-N-oxide

Product 1

HCID 866715014-acetyloxy-2,2,6,6-tetramethylpiperidine-N-oxideYield 78.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution in which 30.3 g (300 mmol) of triethylamine and 34.4 g (200 mmol) of 4-hydroxy-2,2,6,6-tetramethylpiperidine-N-oxide (TEMPOL) were dissolved in 200 mL of tetrahydrofuran (THF), 25.5 g (250 mmol) of acetic anhydride was added at 0° C. The temperature was raised to 25° C. to carry out a reaction for 12 hours, and it was then concentrated by a rotary evaporator. The residue was supplied to 1 liter of iced water, and the precipitated orange solid was collected by filtration to obtain 33.8 g of 4-acetyloxy-2,2,6,6-tetramethylpiperidine-N-oxide.

Workup

  1. customa reaction for 12 hours
  2. concentrationit was then concentrated by a rotary evaporator
  3. filtrationthe precipitated orange solid was collected by filtration

Sources & evidence

ORD record
ord-83f334867a4243d1b1b64e626ad8b412
Source dataset
uspto-grants-2014_12
Patent number
US08912287B2

Reaction notes

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