50675-21-3

Usage

Uses

Used in Pharmaceutical Industry:
1-Methylpiperidine-4-carbaldehyde is used as an intermediate in the synthesis of various pharmaceutical compounds for its reactivity and ability to form a diverse range of products.
Used in Agrochemical Industry:
Similarly, in the agrochemical sector, 1-Methylpiperidine-4-carbaldehyde serves as an intermediate, contributing to the development of a variety of agrochemical products.

InChI:InChI=1/C7H13NO/c1-8-4-2-7(6-9)3-5-8/h6-7H,2-5H2,1H3

Upstream product

• 694-55-3 N-methyl-3,4-didehydropiperidine 
• 201230-82-2 carbon monoxide 
• 1690-75-1 1-methyl-piperidine-4-carboxylic acid methyl ester 
• 71985-80-3 1-methylpiperidine-4-carboxylic acid hydrochloride 
• 872-85-5 pyridine-4-carbaldehyde 
• 24252-37-7 ethyl 1-methylisonipecotate 
• 112391-04-5 4-(1,3-dioxolan-2-yl)-1-methylpiperidine 
• 1445-73-4 1-Methyl-4-piperidone 
• 498-94-2 isonipecotic acid 
• 58795-05-4 4-(1,3-dioxolan-2-yl)-1-methylpyridinium iodide 
• 61379-59-7 4-[1,3]dioxolan-2-yl-pyridine 

Downstream Products

• 10333-64-9 1-methyl-4 (formylmethyl)piperidine 
• 1191255-73-8 C₂₄H₃₁N₅O₂ 
• 1383539-74-9 2-(2,5-dimethyl-benzylsulfanyl)-4-(1-methyl-piperidin-4-yl)-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile 
• 111725-58-7 11-(γ-aminopropyl)-3-methyl-3,7,11-triazaspiro<5,6>dodecane 

Relevant academic research and scientific papers

Ligand-biased and probe-dependent modulation of chemokine receptor CXCR3 signaling by negative allosteric modulators

Over the last decade, functional selectivity (or ligand bias) has evolved from being a peculiar phenomenon to being recognized as an essential feature of synthetic ligands that target G protein-coupled receptors (GPCRs). The CXC chemokine receptor 3 (CXCR3) is an outstanding platform to study various aspects of biased signaling, because nature itself uses functional selectivity to manipulate receptor signaling. At the same time, CXCR3 is an attractive therapeutic target in the treatment of autoimmune diseases and cancer. Herein we report the discovery of an 8-azaquinazolinone derivative (N-{1-[3-(4-ethoxy-phenyl)-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidin-2-yl]ethyl}-4-(4-fluorobutoxy)-N-[(1-methylpiperidin-4-yl)methyl]butanamide, 1b) that can inhibit CXC chemokine 11 (CXCL11)-dependent G protein activation over β-arrestin recruitment with 187-fold selectivity. This compound also demonstrates probe-dependent activity, that is, it inhibits CXCL11- over CXCL10-mediated G protein activation with 12-fold selectivity. Together with a previously reported biased negative allosteric modulator from our group, the present study provides additional information on the molecular requirements for allosteric modulation of CXCR3.

SUBSTITUTED SULFONAMIDE COMPOUNDS

Substituted sulfonamide derivatives, a process for their preparation, pharmaceutical compositions containing these compounds, and to the use of substituted sulfonamide derivatives in the treatment or inhibition of pain and/or various disorders or disease states.

Anti-hypertensive piperidine compounds

Novel compounds of the formula: STR1 are described wherein Z is a bicyclic aryl group containing between 9 and 10 ring atoms, up to two of which may be nitrogen and up to one of which may be oxygen or sulfur; A is an ethenyl group which may be lower-alkyl-substituted; and R and R' each represent H or an aliphatic group of 1-4 carbon atoms; or a pharmaceutically acceptable acid addition salt thereof.

Approaches to Protection against Nerve Agent Poisoning. (Naphthylvinyl)pyridine Derivatives as Potential Antidotes

Analogues of the potent inhibitor of choline acetyltransferase (CAT) (E)-4-(1-naphthylvinyl)pyridine methiodide were synthesized and evaluated for their ability to inhibit CAT and protect against nerve agent intoxication.Several compounds, notably (E)-1-(2-hydroxyethyl)-(1-naphthylvinyl)pyridinium bromide (3), (E)-1-methyl-4-(1-naphthylvinyl)-1,2,3,6-tetrahydropyridine hydrochloride (22), and (E)-1-methyl-4-(1-naphthylvinyl)piperidine hydrochloride (23), were found to afford significant protection against sarin in the mouse and against soman in the giunea pig.However, protection was apparently not related to CAT inhibition.Compound 23, our most effective compound in protecting against nerve agent, was without CAT inhibitory activity.Compound 22, which proved to be a potent CAT inhibitor, most likely owed this activity to being dehydrogenated back to the pyridinium quaternary salt by oxidative enzymes.Several of the (naphthylvinyl)pyridine quaternary salts, but not their tertiary amine analogues, were found to be effective in slowing the rate of aging of soman-inhibited acetylcholinesterase.Ability to slow the rate of aging was enhanced by introduction of methoxy substituents on the aryl moiety whereas the aging rate was actually accelerated by chloro substituents.To date, our most effective compound in slowing the rate of aging, (E)-4-pyridine methochloride (6), did not provide significant protection against soman in the mouse.

Synthesis of 1'-Methylspiro from 1-Methyl-n-piperidinecarbaldehydes

1'-Methylspiro 2 can be obtained from 1-methyl-n-piperidinecarbaldehydes 1 by the Fischer reaction of their phenylhydrazones.The Fischer reaction provides different kinds of products -3H-indole, indole and oxindole- which depend on the N atom position in the piperidine ring.

Hydroformylation of Nitrogen-Containing Cyclic Olefins via "in-situ" Rhodium-Phosphine Catalysts

Hydroformylation of nitrogen-containing cyclic olefins (N-substituted nortropidines, N-methyl-1,2,3,6-tetrahydropyridine (THP)) with rhodium-PR3 catalysts prepared "in-situ" is reported.The nortropidines reacted rapidly when either trialkyl- or triaryl-type phosphines were used, and the regioselectivities were not significantly influenced by the nature of the phosphine.With the less basic THP the rates and selectivities were generally lower, and were influenced by the phosphine ligand and by the presence of added bases such as Et3N.