13290-48-7

Usage

Uses

Used in Pharmaceutical Research:
1-(3-Methylbenzoyl)piperidine is used as a key compound in pharmaceutical research for the development of new drugs and therapeutic agents. Its unique structure and potential biological activities make it a valuable candidate for creating innovative medications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1-(3-Methylbenzoyl)piperidine is employed as a building block for designing and synthesizing new molecules with potential medicinal properties. Its structural versatility allows for the creation of a wide range of compounds with diverse pharmacological effects.
Used in Psychoactive Agent Development:
1-(3-Methylbenzoyl)piperidine is used as a potential psychoactive agent due to its structural similarities with known psychoactive compounds. Its effects on the central nervous system are yet to be fully explored, but it holds promise for the development of new treatments for various psychiatric and neurological disorders.
Used in Analgesic Agent Development:
As a potential analgesic agent, 1-(3-Methylbenzoyl)piperidine is investigated for its ability to alleviate pain. Its specific mechanism of action and efficacy in pain management are areas that require further research and development.

InChI:InChI=1/C13H17NO/c1-11-6-5-7-12(10-11)13(15)14-8-3-2-4-9-14/h5-7,10H,2-4,8-9H2,1H3

Upstream product

• 110-89-4 piperidine 
• 1711-06-4 3-Methylbenzoyl chloride 
• 587-03-1 3-methylbenzyl alcohol 
• 313549-89-2 (1H-benzo-[d][1,2,3]triazol-1-yl)(m-tolyl)methanone 
• 620-23-5 m-tolyl aldehyde 
• 36718-84-0 4-nitrophenyl 3-methylbenzoate 

Downstream Products

• 672295-87-3 3-(piperidine-1-carbonyl)-benzaldehyde 

Relevant academic research and scientific papers

An efficient method for the preparation of styrene derivatives via Rh(III)-catalyzed direct C-H vinylation

The development of a method for the Rh(III)-catalyzed direct vinylation of an aromatic C-H bond to give functionalized styrenes in good yield, using vinyl acetate as a convenient and inexpensive vinyl source, is reported. High functional group tolerance is demonstrated for electronically distinct arenes as well as different directing groups. Mechanistic investigation resulted in the characterization of a novel rhodium-metallacycle, which represents the first X-ray structure of a [1,2]-Rh(III)-alkenyl addition adduct.

Kinetic study on aminolysis of 2-chloro-4-nitrophenyl x-substituted-benzoates in acetonitrile and in H2O Containing 20mol% DMSO: Effects of medium and substituent X on reactivity and reaction mechanism

Second-order rate constants for reactions of 2-chloro-4-nitrophenyl X-substituted-benzoates 1a-1j with a series of cyclic secondary amines in MeCN have been measured. Comparison of the kinetic results with those reported previously for the corresponding reactions carried out in H2O containing 20 mol % DMSO has revealed that amines are less reactive in MeCN. The Bronsted-type plot for the aminolysis of 2-chloro-4-nitrophenyl benzoate (1f) in MeCN is linear with βnuc= 0.64, which is in contrast to the curved Bronsted-type plot reported for the reaction performed in the H2O-DMSO misxture. The Hammett plot for the reactions of 1a-1j with piperidine consists of two intersecting straight lines while the Yukawa-Tsuno plot exhibits an excellent linear correlation with ρX= 1.22 and r = 0.60, indicating that the nonlinear Hammett plot is not due to a change in rate-determining step but is caused by stabilization of substrates possessing an electron-donating substituent through resonance interactions between the substituent and the carbonyl functionality. It has been concluded that medium change from the H2O-DMSO mixture to MeCN forces the aminolysis of 1a-1j to proceed through a concerted mechanism by destabilizing the zwitterionic tetrahedral intermediate (T±).

METHODS OF CONTROLLING CROP PESTS USING AROMATIC AMIDE INSECT REPELLENTS, METHODS OF MAKING AROMATIC AMIDE INSECT REPELLENTS, AND NOVEL AROMATIC AMIDE INSECT REPELLENTS

Methods of protecting fruit crops from flying insect pests and of repelling flying insects using aromatic amide compounds are disclosed. The methods apply the compounds to various surfaces, such as the fruit crops, the ground or structures adjacent to the fruit crops, or an object, article, human skin or animal. The compounds have the formula RxC6Hy—C(═O)—N(Cy), where RxC6Hy is a substituted phenyl group, each R group is independently C1-C6 alkyl, substituted C1-C4 alkyl, (substituted) C6-C10 aryl, C1-C4 alkoxy, C6-C10 aryloxy, halogen, nitro, cyano, cyanate, isocyanate, nitroso, C1-C4 alkylthio, phenylthio, (halogen-substituted) C1-C4 alkylsulfonyl, phenylsulfonyl, tolylsulfonyl, amino, mono- or di-C1-C4 alkylamino, diphenylamino, di-C1-C4 alkylamido, formyl, C2-C7 acyl, or C1-C6 alkoxycarbonyl; x is an integer of 1 to 5; x+y=5; Cy is a C2-C8 (substituted) alkadiyl, a C4-C6 (substituted) alkenediyl, or a (substituted) diyl of the formula —(CH2CH2)—O—(CH2CH2)—, —(CH2CH2)—NR′—(CH2CH2)— or —(CH2CH2)—S—(CH2CH2)— that, along with the amide N atom, forms a non-aromatic cyclic group; and R′ is C1-C6 alkyl, substituted C1-C4 alkyl, (substituted) C6-C10 aryl, or (substituted) benzyl.

Novel synthesis of benzotriazolyl alkyl esters: an unprecedented CH2insertion

We have developed a novel method for the synthesis of benzotriazolyl alkyl esters (BAEs) fromN-acylbenzotriazoles and dichloromethane (DCM) under mild conditions. This reaction is one of few examples to show the use of DCM as a C-1 surrogate in carbon-heteroatom bond formation and to highlight the versatility of using DCM as a methylene building block.

Copper-Catalyzed Aerobic Oxidative Amidation of Benzyl Alcohols

A Cu-catalyzed synthesis of amides from alcohols and secondary amines using the oxygen in air as the terminal oxidant has been developed. The methodology is operationally simple requiring no high pressure equipment or handling of pure oxygen. The commercially available, nonprecious metal catalyst, Cu(phen)Cl2, in conjunction with di-tert-butyl hydrazine dicarboxylate and an inorganic base provides a variety of benzamides in moderate to excellent yields. The pKa of amine conjugate acid and electronics of alcohol were shown to impact the selection of base for optimal reactivity. A mechanism consistent with the observed reactivity trends, KIE, and Hammett study is proposed.

Kinetic study on aminolysis of y-substituted-phenyl x-substituted- benzoates: Effects of substituents x and y on reactivity and reaction mechanism

A kinetic study on aminolysis of 2-chloro-4-nitrophenyl X-substituted-benzoates (2a-k) in 80 mol % H2O/20 mol % DMSO at 25.0 oC is reported. The Bronsted-type plot for the reactions of 2-chloro-4-nitrophenyl benzoate (2g) with a series of cyclic secondary amines curves downward (e.g., β1 = 0.25, β2 = 0.85 and pKa o = 10.3), which is typical of reactions reported to proceed through a stepwise mechanism with a change in ratedetermining step (RDS). The Hammett plot for the reactions of 2a-k with piperidine consists of two intersecting straight lines, while the corresponding Yukawa-Tsuno plot exhibits an excellent linear correlation with ρX = 1.15 and r = 0.59. Thus, it has been concluded that the nonlinear Hammett plot is not due to a change in RDS but is caused by stabilization of substrates through resonance interactions between the electron-donating substituent and the C=O bond. Substrates possessing a substituent at the 2-position of the leaving aryloxide deviate negatively from the curved Bronsted-type plot for the reactions of Y-substituted-phenyl benzoates (3ai), implying that the steric hindrance exerted by the substituent at the 2-position is an important factor which governs the reactivity of Y-substituted-phenyl benzoates.

Aerobic oxidative amidation of aromatic and cinnamic aldehydes with secondary amines by CuI/2-pyridonate catalytic system

A simple and convenient CuI/2-pyridonate catalytic system for the oxidative amidation of aldehydes with secondary amines has been developed. With this system, a variety of useful arylamides have been synthesized in moderate to good yields in the presence of small amount of copper catalyst and the pyridonate ligand, generating only water as a coproduct. Synthesis of cinnamamides was also achieved by the reactions of cinnamaldehydes with secondary amines in moderate yields. Air was successfully employed as a green oxidant in this catalytic system, achieving a safe and atom-efficient system for the synthesis of amides.

Effect of Acyl Substituents on the Reaction Mechanism for Aminolyses of 4-Nitrophenyl X-Substituted Benzoates

Second-order rate constants (kN) have been measured spectrophotometrically for the reaction of 4-nitrophenyl X-substituted benzoates with a series of alicyclic secondary amines in H2O containing 20 mol % dimethyl sulfoxide at 25.0°C.