1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine → HCID 12116356, compound

HRID 1265940Notes

Reaction equation

HRID 1265940 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5](O)[CH2:4][C:3]1([CH3:12])[CH3:11].N(OC(C)(C)C)=O.[C:20]1([C:26](=[CH2:36])[CH2:27][O:28][C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2N)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>N1C=CC=CC=1>[C:20]1([C:26]2([CH2:36][O:1][N:2]3[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]3([CH3:12])[CH3:11])[C:30]3[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=3[O:28][CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 10906Tert-Butyl nitriteHCID 18547258HCID 18547258, compound

Product 1

HCID 12116356HCID 12116356, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

The procedure of Example 1 is repeated using 3.9 g (25 mmol) of 1-oxyl-2,2,6,6-tetramethyl-4-hydroxypiperidine, 6.18 g (60 mmol) of tert-butyl nitrite, 15 mg (0.025 mmol) of (S,S)-(+)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) mmol) in 100 mL of pyridine and 11.25 g (50 mmol) of 2-(2-phenylallyloxy)-aniline in 20 mL of pyridine. The crude product obtained is purified by liquid chromatography (2.5% ethyl acetate/heptane) to give 2.5 g of an off-white oil in 27.4% yield. MS [M+1] 366

Workup

  1. customThe crude product obtained
  2. customis purified by liquid chromatography (2.5% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-6a61e229f6fc4d1db6d6d9ca04142cb0
Source dataset
uspto-grants-2003_04
Patent number
US06547841B2

Reaction notes

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