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Thermochemical properties of three piperidine derivatives

1-benzyl-4-piperidinol, 4-benzylpiperidine and 4-piperidine-piperidine

Journal of Thermal Analysis and Calorimetry
Authors: M. Ribeiro da Silva and Joana Cabral

Abstract  

The standard (p o=0.1 MPa) molar energies of combustion for the crystalline 1-benzyl-4-piperidinol and 4-piperidine-piperidine, and for the liquid 4-benzylpiperidine, were measured by static bomb calorimetry, in oxygen, at T=298.15 K. The standard molar enthalpies of sublimation or vaporization, at T=298.15 K, of these three compounds were determined by Calvet microcalorimetry. Those values were used to derive the standard molar enthalpies of formation, at T=298.15 K, in their condensed and gaseous phase, respectively.

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This paper reports an investigation of physicochemical properties of four series of carbamates of 3-hydroxy and 4-hydroxyphenyl-acetamides of 4-benzylpiperidine and 1-benzylpiperazine which act as inhibitors of acetyl- and butyryl-cholinesterases. Two experimental methods, reversed-phase high-performance liquid chromatography (RP-HPLC) and reversed-phase thin-layer chromatography (RPTLC), were used to determine the lipophilicity of the selected compounds. The results obtained were compared with theoretical lipophilicity calculated by use of ChemOffice, QikProp, and Pallas software. Correlation with the experimental data was the best for log P COMB values calculated with Pallas and QPlog P calculated with QikProp. The QikProp software was also used to estimate several physicochemical properties for all the compounds; these were then used for preliminary analysis of quantitative structure-activity relationships.

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