Synthesis of 3-Aryl-1-adamantanemethylamines

Article abstract of DOI:10.1021/je00036a037

Friedel-Crafts alkylations of fluorobenzene, thioanisole, and thiophene with 3-bromo-1-adamantanecarboxylic acid are reported.Various Lewis acids (AlCl3, FeCl3, ZnCl2, SnCl4) served as effective catalysts for these substitution reactions.The products were 3-aryl-1-adamantanecarboxylic acids.Substitution took place in fluorobenzene and thioanisole at the para position and in thiophene at positions 2 and 3.These acids were reacted with phosphorus pentachloride and then ammonia to form amides which were reduced by lithium aluminum hydride to provide the corresponding3-aryl-1-adamantanemethylamines.