68453-37-2

Usage

Uses

Used in Pharmaceutical Synthesis:
METHYL 4-(PIPERIDIN-1-YLMETHYL)BENZOATE is used as an intermediate in the production of various chemical compounds and drugs, leveraging its unique structure to facilitate the synthesis process and contribute to the development of new medicinal products.
Used in Biochemical Research:
As an enzyme inhibitor, METHYL 4-(PIPERIDIN-1-YLMETHYL)BENZOATE is utilized in biochemical research to study its effects on specific enzymes, potentially leading to advancements in understanding enzyme functions and the development of targeted therapies.
Used in Pharmaceutical Industry:
METHYL 4-(PIPERIDIN-1-YLMETHYL)BENZOATE is used as a key component in the formulation of new drugs, taking advantage of its chemical properties to enhance the efficacy and safety of pharmaceutical products.
Used in Organic Chemistry:
In the field of organic chemistry, METHYL 4-(PIPERIDIN-1-YLMETHYL)BENZOATE serves as a versatile building block for the synthesis of complex organic molecules, contributing to the discovery of novel compounds with potential applications in various industries.

InChI:InChI=1/C14H19NO2/c1-17-14(16)13-7-5-12(6-8-13)11-15-9-3-2-4-10-15/h5-8H,2-4,9-11H2,1H3

Upstream product

• 1571-08-0 methyl 4-formylbenzoate 
• 660-88-8 5-aminopentanoic acid 
• 6757-32-0 4-(piperidine-1-carbonyl)benzoic acid methyl ester 
• 619-66-9 4-Carboxybenzaldehyde 
• 1314659-42-1 4-formyl-N,N-bis(pyridin-2-ylmethyl)benzamide 
• 67-56-1 methanol 
• 1314659-61-4 4-(piperidin-1-ylmethyl)-N,N-bis(pyridin-2-ylmethyl)benzamide 
• 110-89-4 piperidine 
• 2417-72-3 Methyl 4-(bromomethyl)benzoate 
• 34040-64-7 p-methyloxycarbonylbenzyl chloride 

Downstream Products

• 768320-30-5 4-(piperidin-1-ylmethyl)benzoyl chloride 
• 159691-33-5 4-(piperidin-1-ylmethyl)benzoic acid 
• 1350648-07-5 2,3-diamino-N₂-(4-(piperidin-1-ylmethyl)benzyl)quinoxaline 
• 1350648-02-0 N-(3-aminoquinoxalin-2-yl)-4-(piperidin-1-ylmethyl)benzamide 

Relevant academic research and scientific papers

Hydrosilylative reduction of primary amides to primary amines catalyzed by a terminal [Ni-OH] complex

A terminal [Ni-OH] complex1, supported by triflamide-functionalized NHC ligands, catalyzes the hydrosilylative reduction of a range of primary amides into primary amines in good to excellent yields under base-free conditions with key functional group tolerance. Catalyst1is also effective for the reduction of a variety of tertiary and secondary amides. In contrast to literature reports, the reactivity of1towards amide reduction follows an inverse trend,i.e., 1° amide > 3° amide > 2° amide. The reaction does not follow a usual dehydration pathway.

Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application

Developing mild and efficient catalytic methods for the selective synthesis of amines is a longstanding research objective. In this respect, catalytic deoxygenative amide reduction has proven to be promising but challenging, as this approach necessitates selective C–O bond cleavage. Herein, we report the selective hydroboration of primary, secondary, and tertiary amides at room temperature catalyzed by an earth-abundant-metal catalyst, Zr-H, for accessing diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C–N bond cleavage-reformation process, followed by C–O bond cleavage.

Discovery and Structural Optimization of 4-(Aminomethyl)benzamides as Potent Entry Inhibitors of Ebola and Marburg Virus Infections

The recent Ebola epidemics in West Africa underscore the great need for effective and practical therapies for future Ebola virus outbreaks. We have discovered a new series of remarkably potent small molecule inhibitors of Ebola virus entry. These 4-(aminomethyl)benzamide-based inhibitors are also effective against Marburg virus. Synthetic routes to these compounds allowed for the preparation of a wide variety of structures, including a conformationally restrained subset of indolines (compounds 41-50). Compounds 20, 23, 32, 33, and 35 are superior inhibitors of Ebola (Mayinga) and Marburg (Angola) infectious viruses. Representative compounds (20, 32, and 35) have shown good metabolic stability in plasma and liver microsomes (rat and human), and 32 did not inhibit CYP3A4 nor CYP2C9. These 4-(aminomethyl)benzamides are suitable for further optimization as inhibitors of filovirus entry, with the potential to be developed as therapeutic agents for the treatment and control of Ebola virus infections.

Iron-Catalysed Reductive Amination of Carbonyl Derivatives with Ω-Amino Fatty Acids to Access Cyclic Amines

An efficient method for the reductive amination of carbonyl derivatives with ω-amino fatty acids catalysed by an iron complex Fe(CO)4(IMes) [IMes=1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene] by means of hydrosilylation was developed. A variety of pyrrolidines, piperidines and azepanes were selectively synthesised in moderate-to-excellent yields (36 examples, 47–97 % isolated yield) with a good functional group tolerance.

BENZAMIDE DERIVATIVES FOR INHIBITING ENDOPLASMIC RETICULUM (ER) STRESS

Novel 3-(N-piperidinyl)methyl benzamide derivatives are disclosed. The compounds can be used in treating diseases and conditions which are associated with abnormal cell function related to endoplasmic reticulum (ER) stress. For example, the compounds can

HISTONE DEACETYLASE INHIBITORS

Provided herein are compounds and methods for inhibiting histone deacetylase ("HDAC") enzymes (e.g., HDAC1, HDAC2, and HDAC3).

Photoredox-catalyzed Direct Reductive Amination of Aldehydes without an External Hydrogen/Hydride Source

The direct reductive amination of aromatic aldehydes has been realized using a photocatalyst under visible light irradiation. The single electron oxidation of an in situ formed aminal species generates the putative α-amino radical that eventually delivers the reductive amination product. This method is operationally simple, highly selective, and functional group tolerant, which allows the direct synthesis of benzylic amines by a unique mechanistic pathway.

Discovery of a Benzamide Derivative That Protects Pancreatic β-Cells against Endoplasmic Reticulum Stress

Endoplasmic reticulum (ER) stress-mediated pancreatic insulin-producing β-cell dysfunction and death are critical elements in the onset and progression of both type 1 and type 2 diabetes. Here, through cell-based high throughput screening we identified be

Chelating Bis(1,2,3-triazol-5-ylidene) Rhodium Complexes: Versatile Catalysts for Hydrosilylation Reactions

NHC-rhodium complexes (NHC=N-heterocyclic carbenes) have been widely used as efficient catalysts for hydrosilylation reactions. However, the substrates were mostly limited to reactive carbonyl compounds (aldehydes and ketones) or carbon-carbon multiple bonds. Here, we describe the application of newly-developed chelating bis(tzNHC)-rhodium complexes (tz=1,2,3-triazol-5-ylidene) for several reductive transformations. With these catalysts, the formal reductive methylation of amines using carbon dioxide, the hydrosilylation of amides and carboxylic acids, and the reductive alkylation of amines using carboxylic acids have been achieved under mild reaction conditions.

Combination of 4-anilinoquinazoline, arylurea and tertiary amine moiety to discover novel anticancer agents

In present study, 4-anilinoquinazolines scaffold, arylurea and tertiary amine moiety were combined to design, synthesize gefitinib analogs and discover novel anticancer agents. A series of 4-anilinoquinazoline derivatives (1, 2, 3 and 4) bearing arylurea and tertiary amine moiety at its 6-position were synthesized. Their antiproliferative activities in vitro were evaluated via MTT assay against A431 cell and A549 cell. The SAR of the title compounds was discussed. The compounds 2d, 2i and 2j with potent antiproliferative activities were evaluated their inhibitory activity against EGFR-TK. Compound 2j displayed potent inhibitory activity against EGFR-TK. In addition, compound 2j, at 50 mg/kg, can completely inhibit cancer growth in established nude mouse A549 xenograft model in vivo. These results suggest that the 4-anilinoquinazoline derivatives bearing diarylurea and tertiary amino moiety at its 6-position can serve as anticancer agents and EGFR inhibitors.