1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine → 1-(2,4-Dibromophenoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidine

HRID 1369339Notes

Reaction equation

HRID 1369339 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]1([CH3:12])[CH3:11].N(OC(C)(C)C)=O.[Br:20][C:21]1[CH:27]=[C:26]([Br:28])[CH:25]=[CH:24][C:22]=1N>[Cu](F)F.N1C=CC=CC=1>[Br:20][C:21]1[CH:27]=[C:26]([Br:28])[CH:25]=[CH:24][C:22]=1[O:1][N:2]1[C:7]([CH3:8])([CH3:9])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]1([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 10906Tert-Butyl nitriteHCID 120042,4-Dibromoaniline

Product 1

HCID 120843041-(2,4-Dibromophenoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidineYield 63.5%

Reagents, catalysts & solvents 2

HCID 522688Copper fluorideCatalystHCID 1049PyridineSolvent

Procedure

The procedure of Example 1 is repeated using 12.8 g (74 mmol) of 1-oxyl-2,2,6,6-tetramethyl-4-hydroxypiperidine, 14.23 g (138 mmol) of tert-butyl nitrite, 0.73 g (0.74 mmol) of copper(II) fluoride, 200 mL of pyridine and 8.56 g (92 mmol) of 2,4-dibromoaniline at 65° C. The crude product obtained is purified by vacuum flash chromatography (5% ethyl acetate/heptane) to give 17 g of the title compound as a yellowish solid solid in 63.5% yield. The structure is confirmed by 1Hnmr analysis.

Workup

  1. customat 65° C
  2. customThe crude product obtained
  3. customis purified by vacuum flash chromatography (5% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-830422f8cde14768a6997ba981aa168c
Source dataset
uspto-grants-2003_06
Patent number
US06579328B2

Reaction notes

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