Li Jia-jun
2012
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Journal
Journal of Changzhou University
Abstract
Trans-4-(N-acetylamido)cyclohexanol is an important precursor for the synthesis of pharmaceutical intermediate,hydrochloride salt of trans-4-aminocyclohexanol.Study of synthesizing trans-4-(N-acetylamido)cyclohexanol by two step processes was reported in this article.Starting material p-aminophenol was initially acetylated with acetic anhydride to yield 4-(N-acetylamido)-p-phenol,subsequent hydrogenation of this aromatic compound catalyzed by 5% Ru/C in presence of alkaline auxiliary at 5.0 MPa and 120 ℃ afforded the mixed trans-and cis-4-(N-acetylamido)cyclohexanol with 96.9% selectivity and 100% reactant conversion.The trans to cis ratio was 78 to 22 monitored by HPLC analysis.The targeted trans-isomer was isolated via recrystallization with 67.0% overall yield.Effects of myriad factors on the catalytic hydrogenation of 4-(N-acetylamido)phenol as well as acetylation of p-aminophenol were investigated.Processes of each synthetic step were monitored by HPLC.The molecular structures of all the products were characterized using infrared and 1H and 13C NMR spectroscopy respectively.