Synthesis, characterization, stereochemistry, antibacterial and antioxidant activity of N-chloroacetyl-2,6-diphenylpiperidines

A new series of N-chloroacetyl-2,6-diphenylpiperidines 13-18 have been synthesized from their corre-sponding piperidines 7-12 . The synthesized compound 14 is unambiguously characterized using IR, mass, 1D and 2D (1H-1H, COSY & 1H-13C, HSQC) NMR spectral techniques and the remaining compounds 13-16 & 18 are characterized by IR, mass and 1D NMR spectra. The NMR spectral data indicate that the com-pound 17 prefers to adopt alternate chair conformation and remaining compounds prefer to adopt boat conformation. The X-ray crystal structure solved for N-chloroacetyl-3-isopropyl-2,6-diphenylpiperidine 16 supports the distorted boat conformation in the solid state. Anti-bacterial evaluation shows that the com-pounds 15 & 16 demonstrate superior activity against all the tested bacteria. All the synthesized com-pounds show promising antioxidant activities compared to the standard BHA (butylated hydroxyanisole).(c) 2023 Elsevier B.V. All rights reserved.

Automated summary

A new series of N-chloroacetyl-2,6-diphenylpiperidines 13-18 were synthesized from piperidines 7-12. Compound 14 was characterized by multiple techniques, while compounds 13-16 & 18 were characterized using specific spectroscopic techniques. NMR data revealed distinct conformations for the compounds, with compound 17 preferring alternate chair conformation and the others preferring boat conformation. The crystal structure of compound 16 supported its distorted boat conformation. Compounds 15 & 16 showed superior antibacterial activity, while all synthesized compounds displayed promising antioxidant activity compared to a standard antioxidant.