Methane → 1-(4-Hydroxyphenyl)-4,4-dimethylpiperidine-2,6-dione

HRID 1179656Notes

Reaction equation

HRID 1179656 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][C:10]1([CH3:18])[CH2:16][C:15](=O)[O:14][C:12](=[O:13])[CH2:11]1.C.O.C(O)C>C(O)C>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([N:1]2[C:12](=[O:13])[CH2:11][C:10]([CH3:18])([CH3:9])[CH2:16][C:15]2=[O:14])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 4034-AminophenolHCID 778133,3-Dimethylglutaric anhydrideHCID 19096565Water ethanol

Product 1

HCID 220477421-(4-Hydroxyphenyl)-4,4-dimethylpiperidine-2,6-dioneYield 50.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
165 °C

Procedure

A mixture of 4-aminophenol (3.27 g, 30.0 mmol) and 3,3-dimethylglutaric anhydride (4.26 g, 30.0 mmol) was heated in a round bottom flask at 165° C. for 1 h, followed by heating at 180° C. for 7 h. After cooling to room temperature the solid material was dissolved in hot ethanol, activated charcoal was added and the solution was heated at reflux for 1 h. The solid material was removed by hot filtration. The solvent was evaporated and the residue was crystallised from water/ethanol yielding the title compound (3.51 g, 50% yield, pink solid).

Workup

  1. temperatureby heating at 180° C. for 7 h
  2. temperatureAfter cooling to room temperature the solid material
  3. temperaturethe solution was heated
  4. temperatureat reflux for 1 h
  5. customThe solid material was removed by hot filtration
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-181426e626a44d35b8dc19f3373fdcc6
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

Loading…