1903-69-1

Basic information

• Product Name: N-METHYLPIPERIDINE-4-CARBOXAMIDE
• Synonyms: N-Methyl-4-piperidinecarboxaMide
• CAS NO: 1903-69-1
• Molecular Formula: C₇H₁₄N₂O
• Molecular Weight: 142.2
• Mol File: 1903-69-1.mol

Chemical Properties

• Melting Point: 123～125℃
• Boiling Point: 318.5°Cat760mmHg
• Flash Point: 149.6°C
• Appearance: /
• Density: 0.997g/cm³
• Vapor Pressure: 0.000361mmHg at 25°C
• Refractive Index: 1.462
• CAS DataBase Reference: N-METHYLPIPERIDINE-4-CARBOXAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-METHYLPIPERIDINE-4-CARBOXAMIDE(1903-69-1)
• EPA Substance Registry System: N-METHYLPIPERIDINE-4-CARBOXAMIDE(1903-69-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1903-69-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
N-METHYLPIPERIDINE-4-CARBOXAMIDE is utilized as a building block in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and agricultural products.
Used in Dye Production:
It serves as an intermediate in the production of dyes, playing a crucial role in the creation of colorants for various applications.
Used in Rubber Chemicals Industry:
N-METHYLPIPERIDINE-4-CARBOXAMIDE is also used as an intermediate in the production of rubber chemicals, enhancing the properties and performance of rubber materials.
Used in Fine Chemicals Industry:
N-METHYLPIPERIDINE-4-CARBOXAMIDE is employed in the synthesis of other fine chemicals, contributing to the development of specialty chemicals for diverse applications.

InChI:InChI=1/C7H14N2O/c1-8-7(10)6-2-4-9-5-3-6/h6,9H,2-5H2,1H3,(H,8,10)

Upstream product

• 6843-37-4 N-methylisonicotinamide 
• 544696-01-7 tert-butyl 4-(methylcarbamoyl)piperidine-1-carboxylate 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 

Downstream Products

• 1400793-97-6 1-[4-(2,3-dihydro-benzo[1,4]dioxin-2-yl)-benzyl]-piperidine-4-carboxylic acid methylamide 
• 1104382-08-2 1-methyl-6-(4-{3-[4-(N-methylaminocarbonyl)-piperidin-1-yl]-propoxy}-3-(trifluoromethyl)-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile trifluoroacetate 
• 1122471-60-6 C₂₅H₃₀F₃N₃O₆S 
• 126579-26-8 4-(N-Methylaminomethyl)piperidine 

Relevant articles and documents

Covalent docking modelling-based discovery of tripeptidyl epoxyketone proteasome inhibitors composed of aliphatic-heterocycles

The potential of specific proteasome inhibitors to act as anti-cancer agents has attracted intensive investigations. The proteasome can be covalently inhibited by epoxyketone derivatives via a two-step reaction. Several computational approaches have been developed to mimic the covalent binding event. Compound 1 composed of a six-membered heterocyclic ring was designed by using covalent docking. With a possible different binding mode from the clinical compound Carfilzomib, it occupied the S5 pocket of 20S proteasome and showed favorable inhibitory activity. Subsequently optimization and evaluation were taken place. Among these compounds, 11h demonstrated extraordinary in vitro inhibitory activity and selectivity, and good in vivo proteasome inhibitory activity, a favorable pharmacokinetic profile and xenograft tumor inhibition. The possible binding pattern of compound 11h against proteasome was further fully explored via calculations, providing a theoretical basis for finding potent proteasome inhibitors.

Discovery of potent, orally bioavailable, small-molecule inhibitors of WNT signaling from a cell-based pathway screen

WNT signaling is frequently deregulated in malignancy, particularly in colon cancer, and plays a key role in the generation and maintenance of cancer stem cells. We report the discovery and optimization of a 3,4,5-trisubstituted pyridine 9 using a high-throughput cell-based reporter assay of WNT pathway activity. We demonstrate a twisted conformation about the pyridine-piperidine bond of 9 by small-molecule X-ray crystallography. Medicinal chemistry optimization to maintain this twisted conformation, cognisant of physicochemical properties likely to maintain good cell permeability, led to 74 (CCT251545), a potent small-molecule inhibitor of WNT signaling with good oral pharmacokinetics. We demonstrate inhibition of WNT pathway activity in a solid human tumor xenograft model with evidence for tumor growth inhibition following oral dosing. This work provides a successful example of hypothesis-driven medicinal chemistry optimization from a singleton hit against a cell-based pathway assay without knowledge of the biochemical target.

PYRIDINE AND PYRIMIDINE BASED COMPOUNDS AS WNT SIGNALING PATHWAY INHIBITORS FOR THE TREATMENT OF CANCER

The present invention relates to pyridine and pyrimidine based compounds, pharmaceutical compositions comprising these compounds and their potential use as therapeutic agents for the treatment and / or prevention of cancer.

Conformations of 1,p-Diazabicycloalkanes (Aza-Belted Piperidines)

Reduction of hexaalkylhydrazine dications produced from 2-methyl-1,2-diazabicyclooctane (4) by alkylation with bis-halides produces diazabicyclo compounds, for which we refer to the nitrogen-containing n atom bridge as the "aza-belt" in the title.The compound having a five-atom belt, 13, exists with a boat piperidine ring having an outward paramidalized nitrogen (13-1), a conclusion based on comparison of observed 1H NMR vicinal coupling constants with those calculated using MM2 geometries.MM2 predicts that 13-1 is favored over otherconformations by at least 2.6 kcal/mol. 13C NMR chemical shifts suggest a gross conformational change between 13 and the six-atom belt compounds, (6) and (10), for which MM2 predicts boat piperidine rings having inward pyramidalized nitrogens.PE and optical spectra of 6 and 13 are discussed. 16, the NH analogue of 13, undergoes unusually facile oxidation to give the aminal 1,5-diazatricyclo5,10>undecane (19).It is concluded from 1H NMR vicinal coupling constants and the unusually high-field absorption of H(3e) and C(3) that 19 exists both its aminal and piperidine six-membered rings in chair conformations, which is also the MM2 prediction.

Facile Reduction of Pyridines with Nickel-Aluminum Alloy

Nickel-aluminum alloy in dilute base can be used to reduce a variety of pyridines, quinolines, and isoquinoline to the corresponding piperidines, 1,2,3,4-tetrahydroquinolines, and 1,2,3,4-tetrahydroisoquinoline in good yield.The reaction is simple to perform, and high temperatures, high pressures, or hydrogen atmospheres are not required.The reaction is accelerated by substituents in the 2-position and by electron-withdrawing groups in the 3- and 4-positions while electron-supplying groups in the 3- and 4-positions retard the reaction.The major product isolated from the reduction of 2-phenylpyridine was 2-cyclohexylpiperidine hydrochloride.With isoniazid (1) and iproniazid (4) the pyridine ring is hydrogenated before the hydrazine is cleaved.