Abstract The N-alkylated 2, 2, 6, 6-tetramethylpiperidin-4-ones 3c–f were prepared from the acetal 6a of triacetonamine (3a) by alkylation followed by hydrolysis of the acetal functionality or alternatively from the corresponding secondary alcohol 2, 2, 6, 6- tetramethylpiperidin-4-ol (7a) by N-alkylation and subsequent oxidation to introduce the ketone unit. Direct alkylation of 3a was only possible by using highly reactive halides such ...