201335-52-6

Upstream product

• 597577-92-9 C₂₁H₂₆N₄S 
• 79-04-9 chloroacetyl chloride 
• 631-61-8 ammonium acetate 
• 104-87-0 4-methyl-benzaldehyde 
• 78-93-3 butanone 

Downstream Products

• 1259568-40-5 C₂₇H₃₀N₄S 
• 1415104-23-2 [Cu₂(2,6-di(p-tolyl)3-methylpiperidin-4-one)Cl₄(H₂O)₃] 
• 1282624-12-7 1-[2-(4-ethoxycarbonylpiperazin-1-yl)acetyl]-3-methyl-2,6-bis(p-methylphenyl)piperidin-4-one 
• 1276544-43-4 3-(3-methyl-2,6-di-p-tolylpiperidin-4-ylideneamino)-2-thioxoimidazolidin-4-one 
• 1268726-06-2 1-(3-chloropropanoyl)-3-methyl-2,6-di(p-tolyl)piperidine-4-one 

Relevant academic research and scientific papers

Cross-linked polystyrene/titanium tetrachloride as a tightly bound complex catalyzed the modified Mannich reaction for the synthesis of piperidin-4-ones

Cross-linked polystyrene beads were prepared, characterized and the resulting polymer carrier was functionalized with titanium tetrachloride (TiCl4)via complexation of polystyrene with TiCl4 to afford the corresponding cross-linked polystyrene-TiCl4 stable complex (PSt/TiCl4)in an one step reaction and characterized by FT-IR, UV, TGA, DSC, XRD, SEM, BET. This tightly bound coordination complex was used as a water tolerant, heterogeneous, recoverable and reusable Lewis acid catalyst for the synthesis of substituted piperidin-4-ones via the modified Mannich multi-component condensation of ketones, aromatic aldehydes, and ammonium acetate in 1:2:1 M ratio under mild conditions. The rate of reactions was found to decrease with an increasing percentage of crosslinking and the mesh size of the copolymer beads. The catalyst is water tolerant, stable and can be easily recovered and reused at least four times without any loss of activity.

Synthesis, stereochemical and biological studies of some N-cyclohexylcarbamoyl -2,6-diarylpiperidin-4-ones

A series of N-cyclohexylcarbamoylpiperidin-4-ones were synthesized by the addition reaction of corresponding piperidin-4-ones with cyclohexylisocyanate in benzene. The structure and stereochemistry of the synthesized N-cyclohexylcarbamoyl -2, 6-diarylpiperidin-4-ones, were established on the basis of their analytical and spectral data (IR, 1H and 13C NMR). 2D NMR spectra (HOMOCOSY, HSQC, HMBC and NOESY) were also recorded to analyze the stereochemistry. In the IR spectra of synthesized compounds, the characteristic absorptions due to ring and amide carbonyl functionalities were observed which evidences the formation of N-cyclohexylcarbamoyl-2, 6-diarylpiperidin-4-ones. NMR spectral results are in line with the proposed structure of the compounds synthesized. Conformational analysis was carried out from the extracted coupling constants and NOESY spectral results. The synthesized compounds were evaluated for their antibacterial and antifungal activities.

Stereoselective synthesis and spectral studies of some benzotriazolylacetyl hydrazones of 3–alkyl–2,6–diarylpiperidin–4–ones

An effort to include biologically potent benzotriazole nucleus into piperidine ring is achieved through hydrazone formation. The characterization of the synthesized compounds was carried out using FT-IR, 1H &13C NMR, 1H–1H COSY, 1H–13C COSY, NOESY spectral techniques and GC-Mass spectrum. The spectral assignments were done without ambiguity using 2D-NMR techniques. The conformational preference of the piperidine ring deduced from the spectral studies is ‘chair’. The diastereotopic nature of the methylene protons/methyl groups present in the molecules is revealed clearly in their spectral pattern observed.

One-Pot Synthesis of Substituted Piperidinones and 3,4-Dihydropyrimidinones Using a Highly Active and Recyclable Supported Ionic Liquid Phase Organocatalyst

1-Ethyl-3-methylimidazolium ethyl sulfate was synthesized and its supported ionic liquid phase form was prepared and used as an organocatalyst for the synthesis of substituted piperidinones and 3,4-dihydropyrimidinones. The ionic liquid was characterized by 1H NMR, 13C NMR, and mass spectrometry. The catalyst is novel, stable, completely heterogeneous, and recyclable for several times and can be easily recovered by filtration. It was characterized with scanning electron microscopy, transmission electron microscopy, thermogravimetric analysis, and energy-dispersive X-ray spectroscopy techniques. The workup procedures are very simple, and products were obtained in good-to-excellent yields with reasonable purities without the need for further chromatographic purification.

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, synthesis and cytotoxicity of novel N-benzylpiperidin-4-one oximes on human cervical cancer cells

A series of fifteen diversified N-benzylpiperidin-4-one oximes were synthesized and characterized by their NMR spectral data. Additionally, single-crystal XRD analysis was performed for the representative symmetrically and unsymmetrically substituted molecules. All the synthesized oximes from unsymmetrical ketones existed as E-isomer as witnessed by their NMR and XRD data. Among the synthesized target compounds that evaluated for their in vitro cytotoxicity against human cervical carcinoma (HeLa) cells, five compounds were potent with IC50 50 of 13.88 μM was found to be the best active compound as depicted by the microscopic analysis.

Synthesis of 4-methyl-N′-(3-alkyl-2r,6c-diarylpiperidin-4-ylidene)-1, 2,3-thiadiazole-5-carbohydrazides with antioxidant, antitumor and antimicrobial activities

The structures of the newly synthesized 4-methyl-N′-(3-alkyl-2r,6c- diarylpiperidin-4-ylidene)-1,2,3-thiadiazole-5-carbohydrazide (5a-5l) were confirmed by spectral and elemental analysis. The difference in the potency of activity against various free radicals, human cancer cells and microbial strains has been evaluated by SAR. Compounds with electron-donating methoxy (5i and 5c) and methyl (5h and 5b) substitutions at the para position of the phenyl showed excellent free radical scavenging effects. In the tested compounds, electron withdrawing fluoro (5k and 5e), chloro (5j and 5d), and bromo (5l and 5f) substitution at the para position of the phenyl ring attached to C-2 and C-6 carbons of the piperidine moiety outperformed cytotoxic and antimicrobial activities. Our findings suggest that the antioxidant, anti-tumor and anti-microbial activities of compounds 5a-5l create promising leads for the development of potent anti-tumor and anti-microbial agents. This journal is the Partner Organisations 2014.

Stereoselective synthesis, spectral and antimicrobial studies of some cyanoacetyl hydrazones of 3-alkyl-2,6-diarylpiperidin-4-ones

A series of novel cyanoacetyl hydrazones of 3-alkyl-2,6-diarylpiperidin-4-ones were synthesized stereoselectively and characterized by IR, Mass, 1H NMR, 13C NMR, 1H-1H COSY and 1H-13C COSY spectra. The stereochemistry of the synthesized compounds was established using NMR spectra. Antimicrobial screening of the synthesized compounds revealed their antibacterial and antifungal potencies. Growth inhibition of Enterobacter Aerogenes by compound 15 was found to be superior to the standard drug.

Synthesis, characterization and antibacterial studies on copper(II) binuclear complexes with substituted piperidin-4-ones

Copper(II) Chloride binuclear complexes with variously substituted 2,6-diphenly piperidin-4-ones [Cu2LCI4(H 2O)3] have been synthesized and characterized by elemental analysis, molar conductance, magnetic suscep

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.