Cumene → 1-Cumyloxy-2,2,6,6-tetramethyl-4-acetyloxypiperidine

HRID 1404318Notes

Reaction equation

HRID 1404318 reaction equation
[C:1]([O:4][CH:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[NH+:8]([O-:13])[C:7]([CH3:15])([CH3:14])[CH2:6]1)(=[O:3])[CH3:2].C(OOC(C)(C)C)(C)(C)C.[C:26]1([CH:32]([CH3:34])[CH3:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[C:32]([O:13][N:8]1[C:9]([CH3:12])([CH3:11])[CH2:10][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:6][C:7]1([CH3:15])[CH3:14])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:34])[CH3:33]

Participants

4

Reactant 3

HCID 7406CumeneHCID 8033Di-tert-butyl peroxideHCID 866715014-acetyloxy-2,2,6,6-tetramethylpiperidine-N-oxide

Product 1

HCID 683151051-Cumyloxy-2,2,6,6-tetramethyl-4-acetyloxypiperidine

Procedure

4.3 g (20 mmol) of 4-acetyloxy-2,2,6,6-tetramethylpiperidine-N-oxide synthesized by the method described in Synthesis Example 1 was dissolved in 20 mL of cumene and 11.7 g (80 mmol) of t-butyl peroxide was added slowly. After a nitrogen bubbling for 30 minutes, it was transferred to a UV laboratory reaction apparatus (System1) made by Heraeus K. K. Light irradiation was performed using a TQ150 type lamp for 10 minutes to carry out a reaction. The reaction mixture was concentrated by a rotary evaporator, and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate=5/1, volume ratio) to obtain 5.5 g of 1-cumyloxy-2,2,6,6-tetramethyl-4-acetyloxypiperidine was obtained (82.3% of yield).

Workup

  1. customdescribed in Synthesis Example 1
  2. customit was transferred to a UV laboratory reaction apparatus (System1)
  3. customLight irradiation
  4. customfor 10 minutes
  5. customa reaction
  6. concentrationThe reaction mixture was concentrated by a rotary evaporator
  7. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate=5/1, volume ratio)

Sources & evidence

ORD record
ord-564abb020fe744229f466cc0d2db7118
Source dataset
uspto-grants-2014_12
Patent number
US08912287B2

Reaction notes

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