Syntheses of a number of (aryl substituted adamantane)alkylamines are described. (I-Aryl-f adamantane)methyl-and ethylamines were prepared in good yields from 4-protoadamantanone. In another sequence, 4-epoxymethyleneprotoadamantane was converted to I-amin*2-(Zphenyl-l-adamantyl)ethane. p(l-Adamantane)benzyI-and phenethylamims were synthesized from 1-(pbromophenyl)adamantane and 1-(p-tolyl)adamantane, respectively. Reaction of chloroacetonitrile with the above amlnes furnished N-substituted 2-chloroacetamidine hydrochlorides, which were the precursors of 2-mercaptoacetamidines and related derivatives. I where a, Ar : C6H5; b, Ar = 4-FC6H4; c, Ar = 4-CH30C6H4; d, Ar = 4-CH3SC6H4 In order to introduce the carbon side chain at C-2 of 8, a number of different approaches were explored. Oxidation of the secondary alcohols (g) with Jones' reagent' provided the ketones, 9. 2,3 Alternate methods were sought for the oxidation of the p-methylthiophenyl alcohol 8 (Ar = p-CH3SC6H4). To avoid oxidation of the sulfide, this alcohol was oxidized by dimethyl sulfoxide and trifluoroacetic anhydride' to provide the corresponding ketone in 96% yield. Ketones were converted readily either to the corresponding methyl-or ethylamines. Reductive cyanation of 9 in a base-catalyzed reaction with p-toluenesulfonylmethyl isocyanide (TOSMIC, van Leusen reagent, 1Ol6 furnished the nitriles 11. The aryl group at C-l caused no particular steric hindrance towards this reaction. Reduction of nitriles 11 with lithium aluminum hydride or borane-dimethyl sulfide complex 7,g tended to be capricious. The most reproducible route to reduce 11 to the primary amines, 13, was to convert 11 first to the corresponding amides 12 by alkaline hydrogen peroxide. 9-11 Smooth reduction of 12 with lithium aluminum hydride led to 12. An alternative procedure, using sodium borohydride and cobaltous chloride reduced the nitriles directly to the primary amines. 12