Phenyl-2-adamantanamine Hydrochloride

2-Phenyl-2-adamantanamine hydrochloride. A solution of 24 g (0.095 mol) of the crude 2-azido-2-phenyladamanatane in 75 mL of 2-propanol is placed in a 1-L beaker fitted with a mechanical stirrer, and heated in a water bath that can be removed quickly. 

active Raney nickel (Notes 3 and 4) is added in portions at 60-70°C with stirring until the evolution of nitrogen ceases (Note 5). The mixture is heated for an additional 10 min, filtered through a Buchner funnel, and washed with 75 mL of 2-propanol in such a manner that the catalyst is always covered with liquid (Note 6). The filtrate is concentrated in a rotary evaporator under reduced pressure. The crude residue is dissolved in 75 mL of toluene and treated with 22 mL of concentrated hydrochloric acid while stirring. The 2-phenyl-2-adamantamine hydrochloride is collected, triturated with 50 mL of warm acetone, filtered again, and air-dried. The yield is 22.5-24.0 g (90-96%), and the product melts at 293-296°C (closed capillary) (Notes 7 and 8). 

2-Adamantanone was obtained from Aldrich Chemical Company, Inc. Active Raney nickel catalyst was obtained from W. R. Grace Company. 

The amount of Raney nickel depends on its hydrogen content. Usually 25-35 g is sufficient. 

The free 2-phenyl-2-adamantanamine may be liberated from the salt by adding a solution of ammonia or sodium hydroxide, extracting with toluene, concentrating, and distilling under reduced 

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Adamantanamine, 2-phenyl-, hydrochloride (8) Tricyclo [3.3.1.13,7]decan-2-amine, 2-phenyl-, hydrochloride (9) (-)... 

Phenyl-2-adamantanamine, 60, 105 2-PHENYL-2-ADAMANTANAM1NE HYDROCHLORIDE, 60, 104 2-Phenyl-2-adamantanol, 60, 105 Phenylchlorodiazirine, 60, 55 PHENYL CYANATE, 61, 35 l-Phenyl-2,2-diethoxycyclopropane, 60, 8 Phenylmercuric acetate, 61, 82... 

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