Aniline → 1-Phenoxy-2,2,6,6-tetramethylpiperidine

HRID 1369337Notes

Reaction equation

HRID 1369337 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]1([CH3:11])[CH3:10].N(OC(C)(C)C)=O.N[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>[Cu](F)F.C(#N)C>[O:1]([N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]1([CH3:11])[CH3:10])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 10906Tert-Butyl nitriteHCID 5499762,2,6,6-Tetramethylpiperidin-1-ol

Product 1

HCID 132131751-Phenoxy-2,2,6,6-tetramethylpiperidineYield 43%

Reagents, catalysts & solvents 2

HCID 522688Copper fluorideCatalystHCID 6342AcetonitrileSolvent

Procedure

The procedure of Example 1 is repeated using 3.9 g (25 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidine, 7.84 g (76 mmol) of tert-butyl nitrite, 25 mg (0.25 mmol) of copper(II) fluoride, 120 mL of acetonitrile and 4.65 g (50 mmol) of aniline at ambient temperature for 72 hours. The crude product is purified by vacuum flash chromatography (heptane) to give 2.5 g of colorless oil in a 43% yield based on nitroxyl.

Workup

  1. customat ambient temperature
  2. customfor 72 hours
  3. customThe crude product is purified by vacuum flash chromatography (heptane)

Sources & evidence

ORD record
ord-f5929db39a18420ca1ac6bb7483d0843
Source dataset
uspto-grants-2003_06
Patent number
US06579328B2

Reaction notes

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