Synthesis and molecular structure analysis of venlafaxine intermediate and its analog

1-(cyano-(4-methoxyphenyl) methyl cyclohexanol(2), C₂₄H₃₂N₂O₂, a Venlafaxine intermediate is found to crystallize in both monoclinic(2a) and orthorhombic(2b) crystal systems. The form2a crystallizes in the space groupC2/c with the cell parametersa = 23.506(3),b = 5.550(3),c = 23.192(3), and β = 115.116(2)^∘.2b crystallizes in space groupP2₁2₁2₁ with cell parametersa = 5.7850(6),b = 11.2680(6), andc = 20.6730(19). The intermolecular hydrogen bonding in the case of the monoclinic polymorph leads to the formation of dimer. The synthesis, characterization, and crystal structure studies of Venlafaxine analog 1-2-1-(4-dimethylamino-phenyl)-ethylideneamino]-1-(4-methoxy-phenyl)-ethyl]-cyclohexanol(4) is reported.4 crystallizes inP―1 space group with cell parametersa = 10.801(7),b = 12.078(7),c = 9.928(5), α = 96.12(5)^∘, β = 110.49(5)^∘, and γ = 112.42(6)^∘.