Utilization of the Sterically Hindered Base, 4-Hydroxy-2,2,6,6-tetramethylpiperidine, as a Hydrogen Halide Acceptor

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Abstract
The synthetic utility of the sterically hindered base, 4-hydroxy-2,2,6,6-tetramethylpiperidine (1) as a hydrogen halide acceptor was studied. It was shown that base 1 can be effectively used in the quaternization reaction of primary aliphatic and aromatic amines to give the corresponding trimethylammonium iodides 2 in 88-98% yield. Base 1 was used also as the dehydrobrominating agent of alkyl and cycloalkyl bromides to give the corresponding unsaturated compounds in 82-95% yield.