1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine → HCID 69035975, compound

HRID 1422184Notes

Reaction equation

HRID 1422184 reaction equation
[H-].[Na+].[OH:3][N:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][CH:7]([OH:12])[CH2:6][C:5]1([CH3:14])[CH3:13].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>O1CCCC1>[OH:3][N:4]1[C:9]([CH3:10])([CH3:11])[CH2:8][CH:7]([O:12][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:6][C:5]1([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 7748Ethyl bromoacetateHCID 24758Sodium hydride

Product 1

HCID 69035975HCID 69035975, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

0.48 g (20 mmol) of sodium hydride is added to a solution of 3.0 g (17 mmol) of 1-oxyl-2,2,6,6-tetramethyl-4-hydroxypiperidine in 25 mL of anhydrous tetrahydrofuran. The reaction mixture is stirred under a blanket of nitrogen for one hour. The mixture is chilled to 0° C. and 2.9 g (17 mmol) of ethyl bromoacetate is added dropwise. After the addition is complete, the reaction is stirred for an additional 30 minutes during which time a white precipitate forms. The mixture is filtered and the solvent is removed under reduced pressure. The title compound is isolated as an orange solid after column chromatography and melts at 41-43° C.

Workup

  1. additionAfter the addition
  2. stirringthe reaction is stirred for an additional 30 minutes during which time a white precipitate forms
  3. filtrationThe mixture is filtered
  4. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-dc5fd29325714f54a758d25f4450793f
Source dataset
uspto-grants-2000_06
Patent number
US06080864

Reaction notes

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