1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine → HCID 12709388, compound

HRID 1265937Notes

Reaction equation

HRID 1265937 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.[CH2:20]([O:23][C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1N)[CH:21]=[CH2:22]>ClC1C=CC=CC=1>[O:23]1[C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[CH:21]([CH2:22][O:1][N:2]2[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]2([CH3:12])[CH3:11])[CH2:20]1

Participants

5

Reactant 3

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 10906Tert-Butyl nitriteHCID 64866392-(ALLYLOXY)ANILINE

Product 1

HCID 12709388HCID 12709388, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

The procedure of Example 1 is repeated using 1.95 g (12.5 mmol) of 1-oxyl-2,2,6,6-tetramethyl-4-hydroxypiperidine, 3.10 g (30 mmol) of tert-butyl nitrite, 7.5 mg (0.012 mmol) of (S,S)-(+)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) mmol) in 100 mL of chlorobenzene and 5.60 g (25 mmol) of 2-allyloxyaniline in 20 mL of chlorobenzene. The crude product obtained is purified by vacuum flash chromatography (25% ethyl acetate/heptane) to give 2.22 g of a viscous liquid in 61.5% yield.

Workup

  1. customThe crude product obtained
  2. customis purified by vacuum flash chromatography (25% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-62e6ed444aa040cca8be4e6e01aef809
Source dataset
uspto-grants-2003_04
Patent number
US06547841B2

Reaction notes

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