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23.2 g. (0.0764 mole) of 4-(1-adamantyloxy)-2-(methylthiomethyl)-aniline was stirred for 2 hours with approximately 96 g. of Raney nickel in 600 ml. of absolute ethanol. The catalyst was filtered and the solvent was evaporated. Purification by chromatography on silica gel followed by recrystallization from CH2Cl2 -Skellysolve B afforded the desired product, a tan solid, m.p. 143.4°-145.1° C. The NMR spectrum was in accord with the assigned structure.

1. filtrationThe catalyst was filtered
2. customthe solvent was evaporated
3. customPurification by chromatography on silica gel
4. customfollowed by recrystallization from CH2Cl2 -Skellysolve B