626-58-4

Usage

Uses

Used in Pharmaceutical Industry:
4-Methylpiperidine is used as a catalyst in the synthesis of stilbene derivatives, which are known for their anti-malarial properties. This application is particularly important in the development of new drugs to combat malaria, a disease that affects millions of people worldwide.
Used in Chemical Industry:
4-Methylpiperidine serves as an anti-corrosive compound for iron, playing a crucial role in protecting metal surfaces from corrosion and extending the lifespan of iron-based structures and equipment.
Used in Peptide Synthesis:
In the field of peptide synthesis, 4-Methylpiperidine is utilized for the removal or deprotection of 9-fluorenylmethyloxycarbonyl (Fmoc) groups. This process is essential for the successful synthesis of peptides, which have a wide range of applications in medicine, biotechnology, and research.

Purification Methods

Purify it via the hydrochloride (m 189o). It is freed from 3-methylpyridine by zone melting. The hydrobromide has m 173o(from butanone/*C6H6). [Beilstein 20 III/IV 1511, 20/4 V 116.]

InChI:InChI=1/C6H13N/c1-6-2-4-7-5-3-6/h6-7H,2-5H2,1H3/p+1

Upstream product

• 108-89-4 picoline 
• 25077-26-3 3-methyl glutarimide 
• 95758-27-3 N-neopentyl-4-(4-methylpiperidinyl)-pyridinium chloride 
• 92886-01-6 N-2-ethylhexyl chloride of 4(4-methylpiperidinyl)pyridine 
• 123-91-1 1,4-dioxane 
• 4457-71-0 3-methylpentane-1,5-diol 
• 100-46-9 benzylamine 
• 858795-25-2 3-methyl-glutaric acid bis-phenethylamide 
• 1453-82-3 isonicotinamide 
• 383865-57-4 4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine 
• 85872-87-3 4-(4-methylpiperidin-1-yl)-benzonitrile 
• 45798-02-5 4-methyl-1-piperidine dithiocarboxylic acid 
• 32049-46-0 sodium 4-methyl-piperidinedithiocarbamate 
• 138163-12-9 benzyl 4-methylene-1-piperidinecarboxylate 

Downstream Products

• 3717-77-9 2-(4-methyl-piperidin-1-yl)-1-phenyl-ethanol 
• 132912-47-1 4,5-Dimethyl-2-(4-methyl-piperidinomethyl)-phenol 
• 349089-67-4 4-methyl-1-phenylacetyl-piperidine 
• 695-15-8 1,4-dimethyl-piperidine 
• 101590-16-3 5-ethyl-5-(4-methyl-piperidino)-barbituric acid 
• 763872-40-8 4-(4-methyl-piperidino)-2,2-diphenyl-butyronitrile 
• 5430-44-4 4-methyl-piperidine-1-sulfonic acid dimethylamide 
• 109805-54-1 (4-methyl-piperidino)-phenyl-acetic acid methyl ester 
• 114160-56-4 (4-methyl-piperidino)-phenyl-acetic acid-(1-ethyl-[3]piperidyl ester) 
• 102071-39-6 4-methyl-1-[3-(4-phenoxymethyl-phenyl)-propyl]-piperidine 
• 102945-73-3 1-[2-(4-methyl-piperidino)-ethyl]-4-phenyl-piperidine-4-carboxylic acid ethyl ester 
• 109156-59-4 (4-methyl-piperidino)-acetic acid-(2,4,6-trimethyl-anilide) 
• 108980-76-3 F₁₇₇₁-0003 
• 17037-68-2 (4-methylpiperidin-1-yl)(phenyl)methanone 

Relevant academic research and scientific papers

PRODUCTION METHOD OF CYCLIC COMPOUND

PROBLEM TO BE SOLVED: To provide an industrially simple production method of a cyclic compound. SOLUTION: A production method of a cyclic compound includes a step to obtain a reduced form (B) by reducing an unsaturated bond in a ring structure of an aromatic compound (A) by means of catalytic hydrogenation of the aromatic compound (A) or its salt using palladium carbon as a catalyst under a normal pressure, in which the aromatic compound (A) has one or more ring structures selected from a group consisting of a five membered-ring, a six membered-ring, and a condensed ring of the five membered-ring or the six membered-ring with another six membered-ring, a hetero atom can be included in the ring structure, and the aromatic compound (A) can have one or two side chains bonded to the ring structure and does not have any carbon-carbon triple bond in the side chain. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Ru subnanoparticles on N-doped carbon layer coated SBA-15 as efficient Catalysts for arene hydrogenation

The N-doped carbon layer coated SBA-15 support has been accomplished via a pyrolysis process. The ultra-low loading Ru nanoparticles (ca. 0.1 wt.%) was incorporated into the support by impregnation and the sequential reduction. The images of HAADF-STEM revealed that the Ru particles with sub-1-nm size (0.2-0.7 nm) were uniformly dispersed on the support. The ultrafine Ru particles displayed the excellent activity for the hydrogenation of olefins, arenes, phenol derivatives and heteroarenes in aqueous phase. The aliphatic or alicyclic compounds were produced selectively without the hydrogenolysis of C–O and C–N bonds. The high turnover frequency (TOF) values can reach up to 10,000 h?1. Notably, the activity of these catalysts improved dramatically with decreasing the sizes of Ru particles. Meanwhile, the N-doped carbon layer coating endowed the high stability of the Ru catalysts and prevented the leaching of the Ru species owning to the strong interaction between doped-N atoms and the ultrafine Ru particles. Overall, this work provides a highly attractive strategy to construct the supported sub-1-nm Ru particles utilized for the aqueous hydrogenation.

Hydrogenation of N-Heteroarenes Using Rhodium Precatalysts: Reductive Elimination Leads to Formation of Multimetallic Clusters

A rhodium-catalyzed method for the hydrogenation of N-heteroarenes is described. A diverse array of unsubstituted N-heteroarenes including pyridine, pyrrole, and pyrazine, traditionally challenging substrates for hydrogenation, were successfully hydrogenated using the organometallic precatalysts, [(η5-C5Me5)Rh(N-C)H] (N-C = 2-phenylpyridinyl (ppy) or benzo[h]quinolinyl (bq)). In addition, the hydrogenation of polyaromatic N-heteroarenes exhibited uncommon chemoselectivity. Studies into catalyst activation revealed that photochemical or thermal activation of [(η5-C5Me5)Rh(bq)H] induced C(sp2)-H reductive elimination and generated the bimetallic complex, [(η5-C5Me5)Rh(μ2,η2-bq)Rh(η5-C5Me5)H]. In the presence of H2, both of the [(η5-C5Me5)Rh(N-C)H] precursors and [(η5-C5Me5)Rh(μ2,η2-bq)Rh(η5-C5Me5)H] converted to a pentametallic rhodium hydride cluster, [(η5-C5Me5)4Rh5H7], the structure of which was established by NMR spectroscopy, X-ray diffraction, and neutron diffraction. Kinetic studies on pyridine hydrogenation were conducted with each of the isolated rhodium complexes to identify catalytically relevant species. The data are most consistent with hydrogenation catalysis prompted by an unobserved multimetallic cluster with formation of [(η5-C5Me5)4Rh5H7] serving as a deactivation pathway.

Cobalt-bridged secondary building units in a titanium metal-organic framework catalyze cascade reduction of N-heteroarenes

We report here a novel Ti3-BPDC metal-organic framework (MOF) constructed from biphenyl-4,4′-dicarboxylate (BPDC) linkers and Ti3(OH)2 secondary building units (SBUs) with permanent porosity and large 1D channels. Ti-OH groups from neighboring SBUs point toward each other with an O-O distance of 2 ?, and upon deprotonation, act as the first bidentate SBU-based ligands to support CoII-hydride species for effective cascade reduction of N-heteroarenes (such as pyridines and quinolines) via sequential dearomative hydroboration and hydrogenation, affording piperidine and 1,2,3,4-tetrahydroquinoline derivatives with excellent activity (turnover number ～ 1980) and chemoselectivity.

Chemoselective reduction of heteroarenes with a reduced graphene oxide supported rhodium nanoparticle catalyst

Rhodium nanoparticles immobilized on reduced graphene oxide were obtained from the microwave-induced thermal decomposition of Rh6(CO)16 in the ionic liquid [bmim][BF4] (bmim = 1-butyl-3-methylimidazolium cation) in the absence of additional stabilizing agents. The resulting rhodium nanoparticles are 99%, without interfering with other reducible groups, and with high conversions. Related catalysts prepared using conventional thermal heating were prepared for comparison purposes and were found to be considerably less active.

NHC-stabilised Rh nanoparticles: Surface study and application in the catalytic hydrogenation of aromatic substrates

New Rh-NPs stabilised by N-Heterocyclic Carbenes (NHC) were synthesized by decomposition of [Rh(η3-C3H5)3] under H2 atmosphere and fully characterized. Surface studies by FT-IR and NMR spectroscopy employing isotopically labelled ligands were also performed. The Rh0.2 NPs are active catalysts in the reduction of various aromatic substrates. In the reduction of phenol, high selectivities to cyclohexanone or cyclohexanol were obtained depending on the reaction conditions. However, this catalytic system exhibited much lower activity in the hydrogenation of substituted phenols. Pyridine was easily hydrogenated under mild conditions and interestingly, the hydrogenation of 4-methyl and 4-trifluoromethylpyridine resulted slower than that of 2-methylpyridine. The hydrogenation of 1-(pyridin-2-yl)propan-2-one provided the β-enaminone 13a in high yield as a consequence of the partial reduction of the pyridine ring followed by isomerization. Quinoline could be either partially hydrogenated to 1,2,3,4-tetrahydroquinoline or fully reduced to decahydroquinoline by adjusting the reaction conditions.

A Rhodium Nanoparticle-Lewis Acidic Ionic Liquid Catalyst for the Chemoselective Reduction of Heteroarenes

We describe a catalytic system composed of rhodium nanoparticles immobilized in a Lewis acidic ionic liquid. The combined system catalyzes the hydrogenation of quinolines, pyridines, benzofurans, and furan to access the corresponding heterocycles, important molecules present in fine chemicals, agrochemicals, and pharmaceuticals. The catalyst is highly selective, acting only on the heteroaromatic ring, and not interfering with other reducible functional groups.

NRF2 REGULATORS

Provided are aryl analogs，pharmaceutical compositions containing them and their use as NRF2 regulators.

Mechanisms of acid decomposition of dithiocarbamates. 5. Piperidyl dithiocarbamate and analogues

(Chemical Equation Presented) In this work, the acid cleavage at 25°C in 20% v/v aqueous ethanol of a series of analogues of piperidine dithiocarbamate X(C2H4)2NCS2 - (X = CH2, CHCH3, NH, NCH3, S, O) was studied. The pH-rate profiles were obtained in the range of Ho -5 and pH 5. They all presented a dumbell shaped curve with a plateau from which the pH-independent first-order rate constant ko (or the specific acid catalysis kH) was calculated, in addition to the acid dissociation constant of the free (pKa) and conjugate acid (pK+) species of the DTC. LFERs of the kinetically determined pKa and pK+ versus pKN (pKa of parent amine) were used to characterize the reactive species and the structure of the transition state of the rate-determining step. For X = CH2, CH3CH the values of kH agree with those of alkDTCs in the strong base region of the Bronsted plot of log kH versus pKN where the transition state is close to a zwitterion formed by intramolecular water-catalyzed S-to-N proton transfer of the dithiocarbamic acid. However, when X = NH, CH3N, O, S, the reactive species is the DTC anion, which is as reactive as an arylDTC, and similarly, the pK+ values correspond to a parent amine that is about 3-4 pK units more basic. The solvent isotope effect indicated that the acid decomposition of these dithiocarbamate anions is specifically catalyzed by a Hydron anchimerically assisted by the heteroatom through a boat conformation.

Efficient Solution-Phase Parallel Synthesis of 4-Substituted N-Protected Piperidines

Practical conditions for the synthesis of 4-substituted N-protected piperidines through CuCN·2LiBr-catalyzed organozinc additions to 1-acylpyridinium salts and subsequent hydrogen-transfer hydrogenation have been established. The reaction sequence is performed at room temperature and provides 4-substituted N-protected piperidines in excellent overall yields without the isolation of intermediate dihydropyridines, In those cases in which the organozinc addition results in mixtures of 2- and 4-substituted dihydropyridines, the 2-substituted isomers are efficiently scavenged with maleic anhydride and subsequently removed by a mild extractive workup with NaHCO3 (sat.). The N-acyl group can conveniently be exchanged from N-phenoxycarbonyl to N-tBoc, thus allowing orthogonal deprotection strategies. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.