Toluene → 1,4-Dihydro-2,6-dimethyl-4-oxo-1-(2,2,6,6-tetramethyl-4-piperidinyl)3-pyridinecarboxylic acid

HRID 464762Notes

Reaction equation

HRID 464762 reaction equation
[CH3:1][C:2]1[O:9][C:7](=[O:8])[CH:6]([C:10]([CH3:12])=O)[C:4](=[O:5])[CH:3]=1.[NH2:13][CH:14]1[CH2:19][C:18]([CH3:21])([CH3:20])[NH:17][C:16]([CH3:23])([CH3:22])[CH2:15]1.C1(C)C=CC=CC=1>O>[CH3:12][C:10]1[N:13]([CH:14]2[CH2:15][C:16]([CH3:23])([CH3:22])[NH:17][C:18]([CH3:21])([CH3:20])[CH2:19]2)[C:2]([CH3:1])=[CH:3][C:4](=[O:5])[C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 1140TolueneHCID 375244-Amino-2,2,6,6-tetramethylpiperidineHCID 122903Dehydroacetic acid

Product 1

HCID 202625521,4-Dihydro-2,6-dimethyl-4-oxo-1-(2,2,6,6-tetramethyl-4-piperidinyl)3-pyridinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 1-liter, 3-neck, round-bottom flask was equipped with a mechanical stirrer, thermometer, and a Dean-Stark water trap topped with a water cooled condenser. The flask was charged with a mixture of 80.5 g (0.479 mol) dehydroacetic acid, 75.0 g (0.479 mol) 4-amino-2,2,6,6-tetramethylpiperidine, and 600 ml toluene. The stirred mixture in the flask was heated to the boiling point by means of an oil bath and the water formed during the reaction was collected in the trap. After 6 hours of reflux a total of 7.0 ml water had been collected and the flask and its contents cooled to room temperature. The mixture deposited crystals on standing which were collected by vacuum filtration. Reduction of volume of toluene in the filtrate caused a deposit of a second crop of crystals. The combined crystals were recrystallized from a 65/35 mixture of hexane/benzene to give 111 g (75.6%) of a white to colorless crystalline solid (M.P. 174° C.). The chemical structure and purity of these crystals were verified by mass spectroscopy, nuclear magnetic resonance spectroscopy; and by elemental analysis.

Workup

  1. customA 1-liter, 3-neck, round-bottom flask was equipped with a mechanical stirrer
  2. temperatureThe stirred mixture in the flask was heated to the boiling point by means of an oil bath
  3. customwas collected in the trap
  4. temperatureAfter 6 hours of reflux a total of 7.0 ml water
  5. customhad been collected
  6. filtrationwere collected by vacuum filtration
  7. customThe combined crystals were recrystallized from a 65/35 mixture of hexane/benzene

Sources & evidence

ORD record
ord-466c70680aab4535acc032aff1d4c2e8
Source dataset
uspto-grants-1985_10
Patent number
US04548973

Reaction notes

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