Water → HCID 86740382, compound

HRID 464764Notes

Reaction equation

HRID 464764 reaction equation
O.[CH3:2][C:3]1O[C:5]([CH3:14])=[CH:6][C:7](=[O:13])[C:8]=1[C:9]([O:11][CH3:12])=[O:10].[NH2:15][CH:16]1[CH2:21][C:20]([CH3:23])([CH3:22])[NH:19][C:18]([CH3:25])([CH3:24])[CH2:17]1>C1(C)C=CC=CC=1>[CH3:2][C:3]1[N:15]([CH:16]2[CH2:17][C:18]([CH3:25])([CH3:24])[NH:19][C:20]([CH3:23])([CH3:22])[CH2:21]2)[C:5]([CH3:14])=[CH:6][C:7](=[O:13])[C:8]=1[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 375244-Amino-2,2,6,6-tetramethylpiperidineHCID 122813714H-Pyran-3-carboxylic acid, 2,6-dimethyl-4-oxo-, methyl ester2×

Product 1

HCID 86740382HCID 86740382, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 500 ml, 3-neck, round-bottom flask is equipped with a mechanical stirrer, thermometer and a Dean-Stark water trap topped with a water cooled condenser. The flask is charged with a mixture of 45.5 g (0.25 moles) of the methyl 2,6-dimethyl-4-oxopyran-3-carboxylate prepared as described above, 39.1 g (0.25 m) 4-amino-2,2,6,6-tetramethylpiperidine, and 300 ml toluene. The stirred mixture in the flask is heated to boiling by means of an oil bath and the water formed during the reaction is collected in the trap. After 4 hours of reflux a total of 3.8 ml water is collected and the flask and its contents are cooled to room temperature. The toluene is removed by means of a rotary evaporator. On standing and cooling the residue deposits crystals of the title product which are further purified by fractional crystallization.

Workup

  1. customA 500 ml, 3-neck, round-bottom flask is equipped with a mechanical stirrer
  2. customprepared
  3. temperatureThe stirred mixture in the flask is heated
  4. customto boiling by means of an oil bath
  5. customis collected in the trap
  6. temperatureAfter 4 hours of reflux a total of 3.8 ml water
  7. customis collected
  8. customThe toluene is removed by means of a rotary evaporator
  9. temperaturecooling the residue deposits crystals of the title product which
  10. customare further purified by fractional crystallization

Sources & evidence

ORD record
ord-b91e894fc53448c599b901580aba0957
Source dataset
uspto-grants-1985_10
Patent number
US04548973

Reaction notes

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