Dioctylamine → 2,2,6,6-Tetramethyl-N,N-dioctylpiperidine-1-carboxamide

Participants

Reaction Steps

To a solution of phosgene in toluene (24.7 ml of a 20% solution, corresponding to 0.05 mol of phosgene) is added dropwise at -30°, within one hour, the solution of 14.2 g (0.1 mol) of 2,2,6,6-tetramethylpiperidine in 25 ml of toluene. Stirring is maintained at 0° for a further 2 hours; there are then added dropwise, within 2 hours, 26.7 g (0.11 mol) of di-n-octylamine in 25 ml of toluene, and the mixture is subsequently stirred for 16 hours at room temperature. In further processing, the salt which has precipitated is filtered off; the filtrate is afterwards repeatedly washed with a small amount of water, dried over sodium sulfate, and the solvent is completely distilled off in a water-jet vacuum. The crude compound is further purified by column chromatography on silica gel (eluant: hexane/diethyl ether 9:1) to obtain the pure 1-di-n-octylcarbamoyl-2,2,6,6-tetramethylpiperidine (compound No. 11) as a viscous liquid; nD20 : 1.4728.

Provenance & Evidence