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Preparation of 1-[2-Amino-1-(4-methoxy-phenyl)-ethyl]-cyclo-hexanol Disclosure Number: IPCOM000008738D
Publication Date: 2002-Jul-08
Document File: 1 page(s) / 19K

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Preparation of 1-[2-Amino-1-(4-methoxy-phenyl)-ethyl]-cyclohexanol by hydrogenation of (1-hydroxy-cyclohexyl)-(4-methoxy-phenyl)-acetonitrile in the presence of nickel catalysts.

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Preparation of 1-[2-Amino-1-(4-methoxy-phenyl)-ethyl]-cyclo-hexanol

1-[2-Amino-1-(4-methoxy-phenyl)-ethyl]-cyclohexanol is an important intermediate in the synthesis of venlafaxine hydrochloride. According to patent US4535186 this intermediate is prepared by hydrogenation of (1-hydroxy-cyclohexyl)-(4-methoxy-phenyl)-acetonitrile in the presence of a rhodium catalyst. These catalysts provide economical drawbacks because of the high price of rhodium. It was now found that with cheap nickel catalysts like Raney-nickel, with or witout pretreatment with a vanadium salt, hydrogenation of (1-hydroxy-cyclohexyl)-(4-methoxy-phenyl)-acetonitrile gives 1-[2-Amino-1-(4-methoxy-phenyl)-ethyl]-cyclo-hexanol in >90% yield. The reaction can be best carried out in an alcohol or dioxan under hydrogen pressure of 20 to 40 bar. The catalyst may be reused several times after filtration of the reaction mixture.