936097-22-2

Upstream product

• 5707-11-9 3,5-dimethyl-2,6-diphenylpiperidin-4-one 
• 79-04-9 chloroacetyl chloride 
• 100-52-7 benzaldehyde 
• 96-22-0 pentan-3-one 

Downstream Products

• 1297599-25-7 1-[2-(1H-imidazol-1-yl)acetyl]-3,5-dimethyl-2,6-diphenyl-piperidin-4-one 

Relevant academic research and scientific papers

Synthesis, conformational preferences and antimicrobial evaluation of N-piperazinoacetyl-r-2,c-6-diphenylpiperidin-4-ones

Five new N-piperazinoacetyl-r-2,c-6-diphenylpiperidin-4-ones 11-15 have been synthesized and characterized using IR, 1H, 13C, DEPT & 2D NMR and mass spectral studies. The NMR spectral data indicate that the N-piperazinoacetyl-r-2,c-6-diphenylpiperidin-4-ones 11-15 prefer to exist in an equilibrium between B1 and B2 conformations. Furthermore, the antibacterial and antifungal studies were carried out. The results show that the piperazinoacetyl piperidin-4-ones 11-15 exhibit good activity against the selected bacterial and fungal strains.

Chemoselective synthesis and spectral studies of N-thiocyanatoacetyl derivatives of 3-alkyl-2,6-diarylpiperidin-4-ones

A series of N–thiocyanatoacetyl derivatives of 3–alkyl–2,6–diarylpiperidin–4–ones has been synthesized by the reaction between the N–chloroacetyl derivatives of the respective piperidin–4–ones and the ambident thiocyanate nucleophile. The synthesized compounds have been characterized through FT–IR,1H,13C,1H–1H COSY,1H–13C COSY and NOESY spectra. The spectral data reveal the conformational priority of the six-membered heterocyclic ring.

Design and synthesis of novel piperazine unit condensed 2,6-diarylpiperidin-4-one derivatives as antituberculosis and antimicrobial agents

A new series of 1-[2-(4-ethoxycarbonylpiperazine-1-yl)acetyl]-2,6- diarylpiperidin-4-ones (3a-3j) has been synthesized by conventional method and were characterized by IR, elemental analysis, mass spectral, 1H NMR, 13C NMR, and single crystal X-ray diffraction analysis. The synthesized compounds were evaluated for their antituberculosis activity against Mycobacterium tuberculosis H37Rv (ATCC-27294) and also its antimicrobial activity were examined against five familiar bacterial and fungal strains. Among the synthesized compounds, compounds 3e-3j exhibit higher inhibition potency (16 μg/ml) against M. tuberculosis H37Rv. Furthermore, compounds containing fluoro substituent in the phenyl ring at C-2 and C-6 positions of the piperidin-4-one motif (compounds 3c, 3d, and 3i) exerted better antibacterial and antifungal activity than the other phenyl-substituted compounds. Springer Science+Business Media, LLC 2011.

Synthesis and spectral characterization of a new class of N-(N-methylpiperazinoacetyl)-2,6-diarylpiperidin-4-ones: Antimicrobial, analgesic and antipyretic studies

A series of N-(N-methylpiperazinoacetyl)-2,6-diarylpiperidin-4-ones (13c-21c) were synthesized by the base catalyzed nucleophilic substitution of N-chloroacetyl-2,6-diarylpiperidin-4-ones obtained from their corresponding 2,6-diarylpiperidin-4-ones with N-methylpiperazine. These newly synthesized compounds were characterized by one- and two-dimensional NMR spectral studies. In all the cases, the piperazine ring adopted normal chair conformation with equatorial orientation of methyl group irrespective of the non-chair conformations of the piperidin-4-one moiety. All the compounds were screened for their possible antibacterial and antifungal activities against a spectrum of microbial agents besides analgesic and antipyretic activities. These biological studies proved that compounds 17c/18c against bacterial and 18c/20c against fungal strains exhibited promising antimicrobial activities whereas 17c/19c and 18c/19c showed beneficial analgesic and antipyretic profiles, respectively, at a concentration of 60 mg/kg and were also found to be more potent than the reference drug.

Synthesis, stereochemistry and antimicrobial evaluation of some N-morpholinoacetyl-2,6-diarylpiperidin-4-ones

In a search for new leads towards potent antimicrobial agents, an array of novel N-morpholinoacetyl-2,6-diarylpiperidin-4-ones has been synthesized and their in vitro antibacterial activity against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi and antifungal activity against Candida albicans, Rhizopus sp., Aspergillus niger and Aspergillus flavus were evaluated. Structure and stereochemistry of all the N-morpholinoacetyl-2,6-diarylpiperidin-4-ones have been analyzed using 1H and 13C NMR spectroscopic techniques. In all the cases, amide N-C{double bond, long}O group is preferentially in coplanar orientation with respect to the dynamically averaged plane of the piperidone ring. Further, all the symmetrically substituted compounds 19, 23, 24, 26 and 27 are expected to adopt half boat conformations while other compounds 20-22 and 25 adopt twist-boat conformations. Structure-activity relationship results for these nine compounds have shown that compounds 26 and 27 exerted excellent antibacterial activity against all the bacterial strains used except 27 against S. aureus. Against C. albicans and A. flavus, compound 24 recorded excellent antifungal activities while against Rhizopus sp., compound 25 showed potent activities. The obtained results may be used as key step for the building of novel chemical compounds with interesting antimicrobial profiles comparable to that of the standard drugs.

Synthesis of novel N-morpholinoacetyl-2,6-diarylpiperidin-4-ones

A series of N-chloroacetyl-2,6-diarylpiperidin-4-ones (10-18) obtained from the corresponding 2,6-diarylpiperidin-4-ones upon base-catalyzed condensation with morpholine afforded N-morpholinoacetyl-2,6-diarylpiperidin-4-ones (19-27). The synthesized compo

Crystal structure and conformation of two similar piperidones

N-Chloroacetyl-3,5-dimethyl-2,6-diphenylpiperidin-4-one(CADMPO),C 21H22Cl NO2, F.W =355.85, monoclinic, P2 1, a= 8.2082(10)A, b = 10.4889(10)A, c= 10.6175(10)A, β= 91.833(10)°, V=913.73(17)A3, Z=2, Dcalc = 1.293Mg/m3, μ = 1.953 mm-1, F000 = 376, CuKα. = 1.5418 A, final R1 and wR2 are 0.0399 and 0.0911, respectively N-Chloroacetyl-3-ethyl-2,6-diphenylpiperidin-4-one (CAEPO), C21H22ClNO2, F.W=355.85, monoclinic, P21/n, a= 10.3626(6)A, b = 8.5702(5)A, c = 21.6930(10)A, β= 92.25(1)°, V= 1925.06(18)A3, Z=8, Dcalc = 1.228Mg/m3, μ = 0.211 mm-1, F000=752, MoKα = 0.71073A, final R1 and wR2 are 0.0623 and 0.1397, respectively. Crystal structure studies of these two 4-piperidones show that the piperidones adopt twist-boat conformation. The C-H... O type of intermodular interactions play a role in stabilizing the molecules in the unit cell in addition to van der Waals forces.