Aniline → HCID 13213174, compound

HRID 1369347Notes

Reaction equation

HRID 1369347 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([O:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][C:3]1([CH3:20])[CH3:19].N(OC(C)(C)C)=O.N[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>[Cu](F)F.N1C=CC=CC=1>[O:1]([N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([O:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][C:3]1([CH3:20])[CH3:19])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 10906Tert-Butyl nitriteHCID 6881781-Hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 13213174HCID 13213174, compoundYield 55,237.102%

Reagents, catalysts & solvents 2

HCID 522688Copper fluorideCatalystHCID 1049PyridineSolvent

Procedure

The procedure of Example 1 is repeated using 5.79 g (0.021 mmol) of 1-oxyl-4-benzoyloxy-2,2,6,6-tetramethylpiperidine, 5.05 g (49 mmol) of tert-butyl nitrite, 12.6 mg (0.125 mmol) of copper(II) fluoride, 120 mL of pyridine and 3.91 g (42 mmol) of aniline at 70° C. The crude product obtained is purified by vacuum flash chromatography (heptane) to give 4.10 g of the title compound as a yellowish oil in 55.3% yield. The structure is confirmed by mass spectrographic analysis. MS [M+1]354.

Workup

  1. customat 70° C
  2. customThe crude product obtained
  3. customis purified by vacuum flash chromatography (heptane)

Sources & evidence

ORD record
ord-78d58ee3870e4a96a959da12a5fcca38
Source dataset
uspto-grants-2003_06
Patent number
US06579328B2

Reaction notes

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