Acetic Anhydride → HCID 21330481, compound

HRID 616550Notes

Reaction equation

HRID 616550 reaction equation
[C:1]([O:9][CH:10]1[CH2:15][C:14]([CH2:17][CH3:18])([CH3:16])[N:13]([CH2:19][CH2:20][OH:21])[C:12]([CH2:23][CH3:24])([CH3:22])[CH:11]1[CH3:25])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:33](OC(=O)C)(=[O:35])[CH3:34]>CN(C)C=O>[C:1]([O:9][CH:10]1[CH2:15][C:14]([CH2:17][CH3:18])([CH3:16])[N:13]([CH2:19][CH2:20][O:21][C:33](=[O:35])[CH3:34])[C:12]([CH2:23][CH3:24])([CH3:22])[CH:11]1[CH3:25])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 21330334HCID 21330334, compound

Product 1

HCID 21330481HCID 21330481, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.5 g of 2,6-diethyl-1-(2-hydroxyethyl)-2,3,6-trimethyl-4-piperidyl benzoate (Compound 45 - prepared following the procedure described in Preparation 9) in 50 ml of dimethylformamide were added 2.0 g of triethylamine and 1 g of acetic anhydride; the mixture was then heated at 80° - 90° C for 5 hours. When the reaction was complete, the reaction mixture was concentrated and 50 ml of benzene were added. The mixture was then washed with, in turn, an aqueous solution of sodium carbonate and water, and was dried over anhydrous sodium sulphate. After removing the solvent, the residue was subjected to distillation under reduced pressure, giving 1.2 g of Compound 50 as a colourless oil (bp 195° C/0.008 mmHg).

Workup

  1. temperaturethe mixture was then heated at 80° - 90° C for 5 hours
  2. concentrationthe reaction mixture was concentrated
  3. addition50 ml of benzene were added
  4. washThe mixture was then washed with, in turn
  5. dry with materialan aqueous solution of sodium carbonate and water, and was dried over anhydrous sodium sulphate
  6. customAfter removing the solvent
  7. distillationthe residue was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-78ef631ce16d414a95c6d390a2229eb5
Source dataset
uspto-grants-1978_02
Patent number
US04075165

Reaction notes

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