Carbon Dioxide → Methyl-bis(2,2,6,6-tetramethylpiperidin-4-yl)amine

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Reaction Steps

) In accordance with the general procedure of Example 1b), the HALS diol (204) is prepared starting from 2-N-morpholino-4,6-bis[N-n-butyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,3,5-triazine (Example yl) with ethylene oxide; m.p. 114°-117° C. Analysis: calcd: C 65.84%; H 10.45%; N 16.60%. found: C 65.86%; H 10.33%; N 16.01%. ##STR61## δ) 1.) 40.48 g (0.14 mol) of bis(2,2,6,6-tetramethylpiperidin-4-yl)amine [EP-A-336 895, Ciba-Geigy] and 11.4 g (0.14 mol) of a 36% aqueous solution of formaldehyde are placed in a 200 ml sulfonation flask. Then 25.8 g (0.56 mol) of formic acid are added dropwise at room temperature. In the course of this addition the temperature in the reactor rises to 70° C., with evolution of CO2. The reaction mixture is then further stirred until it has cooled to room temperature. The aqueous phase is saturated with potassium carbonate and the reaction mixture is extracted 3 times with chloroform. The organic phases are combined, dried over potassium carbonate and concentrated on a vacuum rotary evaporator. Chromatography of the residue on silica gel with the solvent system hexane/dichloromethane 9:1+5% triethylamine yields 21 g (49%) of methyl-bis(2,2,6,6-tetramethylpiperidin-4-yl)amine, m.p. 51°-53° C., as a white powder. 1H-NMR (300 MHz, CDCl3):δ=2.25 ppm (s, 3H) methyl group at the nitrogen.

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