General procedure for the synthesis of 4-cyclohexyl ether-aniline from bromocyclohexane and 1-(cyclohexyloxy)-4-nitrobenzene (CAS: 5493-73-2): to a stirring solution of 1-(cyclohexyloxy)-4-nitrobenzene (1 g) in methanol (15 mL) under nitrogen protection was added 10% Pd/C (0.721 g). The reaction mixture was stirred under a hydrogen atmosphere (using a hydrogen balloon) for 16 hours. Upon completion of the reaction, the mixture was filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure to give the target product 4-cyclohexyl ether-aniline (700 mg). The product was analyzed by LCMS, m/z 192.1 (M + H)+.
