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

HRID 1369340Notes

Reaction equation

HRID 1369340 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.N1C=CC=CC=1.N[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(#N)C.[Cu](F)F>[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:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6115AnilineHCID 10906Tert-Butyl nitriteHCID 5499762,2,6,6-Tetramethylpiperidin-1-ol

Product 1

HCID 132131751-Phenoxy-2,2,6,6-tetramethylpiperidineYield 84.5%

Reagents, catalysts & solvents 2

HCID 522688Copper fluorideCatalystHCID 6342AcetonitrileSolvent2×

Procedure

The process 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 in a mixture of 100 mL of acetonitrile/20 mL of pyridine and 4.65 g (50 mmol) of aniline in 10 mL of acetonitrile at 70° C. The crude product obtained is purified by vacuum flash chromatography (heptane) to give 4.9 g of the title compound as a colorless oil in 84.5% yield.

Workup

  1. customThe crude product obtained
  2. customis purified by vacuum flash chromatography (heptane)

Sources & evidence

ORD record
ord-cb93c460cc2d4d9098b56ddaa277a962
Source dataset
uspto-grants-2003_06
Patent number
US06579328B2

Reaction notes

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