Synthesis and characterization of 1-carbalkoxymethyl-4-hydroxy-1-methylpiperidinium chlorides

Abstract

The synthesis of new 1-carbalkoxymethyl-4-hydroxy-1-methylpiperidinium chlorides derived from 4-hydroxy-1-methylpiperidine and alkyl chloroacetates was described. Salts were characterized by MS, FTIR, 1 H and 13 C NMR spectroscopies. Compounds investigated were tested against Escherichia coli, Staphylococcus aureus, Candida albicans and Aspergillus niger.

Synthesis, Properties, and Antimicrobial Activity of 1-Alkyl-4-hydroxy-1-methylpiperidinium Ionic Liquids with Mandelate Anion

“…Both signals originated from the methyl group attached to the nitrogen atom in the axial or equatorial position. Moreover, it was confirmed that the signal present at the larger chemical shift was derived from the trans isomeric form (Figure A) . On the basis of the integration ratio of these bands, it can be concluded that the molar fraction of the trans form ranges from 49 to 70% (Figure B).…”

“…During the quaternization of 4-hydroxy-1-methylpiperidine, it is possible to obtain two geometrical isomers, since the alkyl substituent can be attached to the nitrogen atom in the cis or trans position relative to the hydroxyl group. This phenomenon has been already described for the homologous series of 1-carbalkoxymethyl-4-hydroxy-1-methylpiperidinium chlorides . Due to their very similar chemical structures as well as analogous physicochemical properties, attempts to separate the isomeric forms of the quaternary precursors using simple laboratory techniques proved to be ineffective.…”

“…Moreover, it was confirmed that the signal present at the larger chemical shift was derived from the trans isomeric form (Figure 1A). 35 On the basis of the integration ratio of these bands, it can be concluded that the molar fraction of the trans form ranges from 49 to 70% (Figure 1B). It is known that in the case of chemical compounds containing six-membered rings substituted in the 1,4 positions, the trans isomer with substituents in equatorial positions is the thermodynamically most stable form.…”

“…This phenomenon has been already described for the homologous series of 1carbalkoxymethyl-4-hydroxy-1-methylpiperidinium chlorides. 35 Due to their very similar chemical structures as well as analogous physicochemical properties, attempts to separate the isomeric forms of the quaternary precursors using simple laboratory techniques proved to be ineffective. Further research is necessary to isolate the individual isomers using advanced methods, to distinguish the properties of the compounds comprising the cis-1-alkyl-4-hydroxy-1-methylpiperidinium and trans-1-alkyl-4-hydroxy-1-methylpiperidinium moieties and to analyze the effect of isomerism on the desired type of activity.…”

Low Molecular Weight Supramolecular Allobetuline-, Cyclohexanol-, or Undecanol-Appended 1,2,3-Triazole-Based Gelators: Synthesis and Molecular Dynamics Simulation Study

“…Physicochemical characteristics of 11 correspond to those described in the literature. 27 Yellow liquid; yield: 6.58 g (91%).…”