Triethylamine → HCID 22153826, compound

HRID 2231941Notes

Reaction equation

[CH2:1]([O:7][CH:8]1[CH2:13][C:12]([CH3:15])([CH3:14])[NH:11][C:10]([CH3:17])([CH3:16])[CH2:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(N(CC)CC)C.[C:25]1([C:31](=[O:35])[C:32](Cl)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl>[CH2:1]([O:7][CH:8]1[CH2:9][C:10]([CH3:16])([CH3:17])[N:11]([C:32](=[O:33])[C:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:35])[C:12]([CH3:15])([CH3:14])[CH2:13]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: -10 °C

Procedure

24.1 g (0.1 mole) of 4-hexyloxy-2,2,6,6-tetramethylpiperidine are dissolved in 100 ml of absolute methylene chloride. To this solution are added 15.2 g (0.15 mole) of absolute triethylamine and the whole solution is cooled to -10° C. At this temperature a solution of 16.8 g (0.1 mole) of phenylglyoxylyl chloride in 100 ml of methylene chloride is slowly added dropwise. When this addition is complete, the reaction mixture is allowed to warm to room temperature and stirred for about 4 hours. Precipitated hydrochloride is removed by filtration and the solution is clarified by filtration over a small amount of silica gel and concentrated by evaporation, affording 28.4 g of 1-(4-hexyloxy-2,2,6,6-tetramethylpiperidino)-2-phenylethane-1,2-dione as a yellow oil (stabiliser 1).

Workup

additionWhen this addition
temperatureto warm to room temperature
customPrecipitated hydrochloride is removed by filtration
filtrationthe solution is clarified by filtration over a small amount of silica gel
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-338ecf6b853d4f8c8114dcb6680273b1
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04785102

Reaction notes

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