M-Xylene → 1-(3-Methylbenzyl)oxy-4-acetamido-2,2,6,6-tetramethylpiperidine

HRID 322796Notes

Reaction equation

HRID 322796 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([NH:10][C:11](=[O:13])[CH3:12])[CH2:4][C:3]1([CH3:15])[CH3:14].[C:16]1([CH3:23])[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=1>>[CH3:23][C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=1)[CH2:22][O:1][N:2]1[C:7]([CH3:8])([CH3:9])[CH2:6][CH:5]([NH:10][C:11](=[O:13])[CH3:12])[CH2:4][C:3]1([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 7929M-XyleneHCID 579904N-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)acetamide

Product 1

HCID 108816961-(3-Methylbenzyl)oxy-4-acetamido-2,2,6,6-tetramethylpiperidineYield 51%

Conditions

Temperature
133 °C

Procedure

A mixture of 10.67 g (0.05 mol) of 1-oxyl-4-acetamido-2,2,6,6-tetramethylpiperidine and 106.17 g (1.0 mol) of m-xylene under a nitrogen atmosphere is heated at 133° C. for 67 hours. The reaction mixture is filtered to remove the hydroxylamine, and the filtrate is washed with 10 w/v % ascorbic acid (3×33 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 4.03 g (51% yield) of a white solid melting at 163-164.5° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customto remove the hydroxylamine
  3. washthe filtrate is washed with 10 w/v % ascorbic acid (3×33 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-4eac0b9138a04f6894cea5c8328d67a5
Source dataset
uspto-grants-2001_04
Patent number
US06211378B1

Reaction notes

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