2-Methyl-5-(4-nitro-phenyl)-2,5-diaza-bicyclo[2.2.1]heptane → 4-(5-Methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)aniline

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Reaction Steps

A mixture of 2-methyl-5-(4-nitro-phenyl)-2,5-diaza-bicyclo[2.2.1]heptane (0.19 g, 0.815 mmol) and a catalytic amount of Pd/C in ethanol (0.2 mL) is hydrogenated at 1 atmosphere at room temperature overnight. It is filtered through Celite, and the organic solution is evaporated, and then treated with 10 mL of methanol. It is then treated with hydrochloric acid in methanol, followed by ethyl ether, and filtered to give 4-(5-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-phenylamine as bluish solid (0.107 g, 65%). MS (ESI) m/z 204.2 (M−H)+1.

Provenance & Evidence