1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine → HCID 10934026, compound

HRID 322792Notes

Reaction equation

HRID 322792 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].[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=1>>[CH:18]1([O:1][N:2]2[C:7]([CH3:8])([CH3:9])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]2([CH3:12])[CH3:11])[CH2:17][CH2:16][CH2:15][CH:14]=[CH:13]1

Participants

3

Reactant 2

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 8079Cyclohexene

Product 1

HCID 10934026HCID 10934026, compoundYield 36%

Conditions

Temperature
70 °C

Procedure

A mixture of 17.05 g (0.10 mol) of 1-oxyl-4-hydroxy-2,2,6,6-tetramethylpiperidine and 100 mL (0.99 mol) of cyclohexene under a nitrogen atmosphere is heated at 70° C. for 72 hours. The reaction mixture is filtered to remove 1,4-dihydroxy-2,2,6,6-tetramethylpiperidine and the filtrate is washed with 5 w/v % ascorbic acid (2×50 mL) and distilled water (2×50 mL). The organic phase is dried over anhydrous sodium sulfate and the volatiles are removed in vacuo. The residue is recrystallized from acetonitrile to give 4.44 g (36% yield) of a white solid melting at 65-66.5° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customto remove 1,4-dihydroxy-2,2,6,6-tetramethylpiperidine
  3. washthe filtrate is washed with 5 w/v % ascorbic acid (2×50 mL)
  4. distillationdistilled water (2×50 mL)
  5. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  6. customthe volatiles are removed in vacuo
  7. customThe residue is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-eb186fe403aa46dcb060a1d0a0315ba1
Source dataset
uspto-grants-2001_04
Patent number
US06211378B1

Reaction notes

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