Tert-Butyl nitrite → 1-(4-Benzoylphenoxy)-2,2,6,6-tetramethylpiperidine

HRID 1369343Notes

Reaction equation

HRID 1369343 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:33]=[CH:32][C:23]([C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])=[CH:22][CH:21]=1>N1C=CC=CC=1.[Cu](F)F>[C:24]([C:26]1[CH:31]=[CH:30][C:29]([O:1][N:2]2[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]2([CH3:11])[CH3:10])=[CH:28][CH:27]=1)(=[O:25])[C:23]1[CH:32]=[CH:33][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 143464-AminobenzophenoneHCID 5499762,2,6,6-Tetramethylpiperidin-1-ol

Product 1

HCID 120843021-(4-Benzoylphenoxy)-2,2,6,6-tetramethylpiperidineYield 80.6%

Reagents, catalysts & solvents 2

HCID 522688Copper fluorideCatalystHCID 1049PyridineSolvent2×

Procedure

The procedure of Example 1 is repeated using 1.95 g (12.5 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidine, 3.92 g (38 mmol) of tert-butyl nitrite, 12.5 mg (0.125 mmol) of copper(II) fluoride, 120 mL of pyridine and 4.93 g (25 mmol) of 4-aminobenzophenone in 40 mL of pyridine at 70° C. The crude product obtained is purified by vacuum flash chromatography (heptane) to give 3.40 g of the title compound as a light yellow oil in 80.6% yield. The structure is confirmed by 1Hnmr, elemental and mass spectrographic analysis.

Workup

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

Sources & evidence

ORD record
ord-82a13a6ef5c44ff0ab99fc66a2f9dc1f
Source dataset
uspto-grants-2003_06
Patent number
US06579328B2

Reaction notes

Loading…