Tert-Butyl nitrite → 4,4'-Bis(2,2,6,6-tetramethylpiperidin-1-yloxy)benzophenone

HRID 1369354Notes

Reaction equation

HRID 1369354 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(O[C:15]([CH3:18])([CH3:17])[CH3:16])=O.N[C:20]1[CH:34]=[CH:33][C:23]([C:24]([C:26]2[CH:31]=[CH:30][C:29](N)=[CH:28][CH:27]=2)=[O:25])=[CH:22][CH:21]=1>N1C=CC=CC=1>[CH3:10][C:3]1([CH3:11])[CH2:4][CH2:5][CH2:6][C:7]([CH3:9])([CH3:8])[N:2]1[O:1][C:20]1[CH:34]=[CH:33][C:23]([C:24]([C:26]2[CH:31]=[CH:30][C:29]([O:1][N:2]3[C:3]([CH3:11])([CH3:10])[CH2:4][CH2:5][CH2:18][C:15]3([CH3:16])[CH3:17])=[CH:28][CH:27]=2)=[O:25])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 691494,4'-DiaminobenzophenoneHCID 5499762,2,6,6-Tetramethylpiperidin-1-ol

Product 1

HCID 225982724,4'-Bis(2,2,6,6-tetramethylpiperidin-1-yloxy)benzophenoneYield 19.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The procedure of Example 1 is repeated using 1.95 g (12.5 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidine, 6.19 g (60 mmol) of tert-butyl nitrite, 7.6 mg (0.0125 mmol) of (S,S)-(+)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II), 80 mL of pyridine and 5.30 g (25 mmol) of 4,4′-diaminobenzophenone at 70° C. The crude product obtained is purified by vacuum flash chromatography (1% ethyl acetate in heptane) to give 0.6 g of the title compound as a yellow solid in 9.17% yield. The structure is confirmed by 1Hnmr and mass spectrographic analysis.

Workup

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

Sources & evidence

ORD record
ord-b74243e140c342fd81911c5d02d40473
Source dataset
uspto-grants-2003_06
Patent number
US06579328B2

Reaction notes

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