1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine → HCID 57120762, compound

HRID 1584548Notes

Reaction equation

HRID 1584548 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].[CH2:13](Br)[CH:14]=[CH2:15].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[OH:1][N:2]1[C:7]([CH3:8])([CH3:9])[CH2:6][CH:5]([O:10][CH2:15][CH:14]=[CH2:13])[CH2:4][C:3]1([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 7841Allyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 57120762HCID 57120762, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A vigorously stirred two phase solution of 30.0 g (0.17 mol) 1-oxyl-2,2,6,6-tetramethyl-4-hydroxypiperidine, 29.0 g (0.24 mol) of allyl bromide, 2.6 g (8 mmol) of tetrabutylammonium bromide, 100 mL of 50% aqueous sodium hydroxide and 30 mL of toluene is heated at 70° C. for 90 minutes. The mixture is partitioned between 100 mL of toluene, 100 mL of heptane and 200 mL of water. The organic phase is dried over anhydrous magnesium sulfate and concentrated to yield the title compound as a red oil after column chromatography.

Workup

  1. customThe mixture is partitioned between 100 mL of toluene, 100 mL of heptane and 200 mL of water
  2. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-aec18d3fa5d544b3a19851d6ee4ef8c7
Source dataset
uspto-grants-1999_08
Patent number
US05932735

Reaction notes

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