Six t(3)-aryl-r(2),c(4)-bisethoxycarbonyl-t(5)-hydroxy-c(5)-methylcyclohexanones (6-11) were synthesized by condensing ArCHO (Ar = Ph, p-O(2)NC(6)H(4), p-CH(3)OC(6)H(4), p-ClC(6)H(4), m-O(2)NC(6)H(4) and m-C(6)H(5)O(6)H(4)) with ethyl acetoacetate in the presence of methylamine and their (1)H and (13)C NMR spectra were recorded. (1)H-(1)H COSY and NOESY spectra were recorded for 6 and 7 and also HSQC and HMBC spectra for 6 and 8. Elemental analysis was carried out for all compounds. The mass spectrum was recorded for 8. All analytical data are consistent with the proposed molecular formulae. Analysis of NMR spectral data suggests that these compounds largely adopt chair conformations with the hydroxyl group occupying an axial orientation and all the other substituents occupying equatorial orientations. Long-range coupling (2-3 Hz) between the OH proton and the axial methylene proton at C-6 is observed in 6, 7, 8 and 11.

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In the title compound, C19H19Cl2N3O2, the piperidine ring adopts a distorted boat conformation. In the solid state, the mol­ecules exist as O—H⋯N‐hydrogen‐bonded centrosymmetric dimers.

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In the title compound, C18H19N3O2·H2O, the piperidine ring adopts a distorted boat conformation. In the solid state, the mol­ecules are linked by inter­molecular O—H⋯O and O—H⋯N hydrogen bonds involving water mol­ecules.