971-34-6

Usage

Uses

Used in Pharmaceutical Industry:
N-[1-(benzyl)-4-piperidyl]benzamide is used as a starting material or intermediate in the synthesis of piperidinyl heterocycles. These heterocycles are of particular interest as they can act as histamine H4 (hD4) receptor ligands, which have potential applications in the treatment of various conditions, including allergies, inflammatory disorders, and autoimmune diseases.
Additionally, as an impurity in Indoramin synthesis, understanding and controlling the presence of N-[1-(benzyl)-4-piperidyl]benzamide can be crucial for ensuring the quality, safety, and efficacy of the final pharmaceutical product. This may involve developing methods for its detection, quantification, and removal or mitigation during the manufacturing process.

InChI:InChI=1/C19H22N2O/c22-19(17-9-5-2-6-10-17)20-18-11-13-21(14-12-18)15-16-7-3-1-4-8-16/h1-10,18H,11-15H2,(H,20,22)

Upstream product

• 50541-93-0 4-amino-1-benzylpiperidine 
• 98-88-4 benzoyl chloride 
• 1315494-51-9 N-(3-fluoropyridin-4-yl)benzamide 
• 2247-88-3 3-fluoro-pyridin-4-ylamine 
• 65-85-0 benzoic acid 
• 959-22-8 p-nitrophenylbenzoate 
• 4783-65-7 N-benzyl-2-piperidinone 

Downstream Products

• 1044-79-7 N-(1-benzylpiperidin-4-yl)-4-chlorobenzamide 
• 974-12-9 N-(1-benzyl-piperidin-4-yl)-4-methyl-benzamide 
• 577778-27-9 1-Acetyl-4-benzamidopiperidin 
• 33953-37-6 N-(piperidin-4-yl)benzamide 

Relevant academic research and scientific papers

Synthesis of a CGRP Receptor Antagonist via an Asymmetric Synthesis of 3-Fluoro-4-aminopiperidine

A practical and efficient enantioselective synthesis of the calcitonin gene-related peptide receptor antagonist 1 has been developed. The key structural component of the active pharmaceutical ingredient is a syn-1,2-amino-fluoropiperidine 4. Two approaches were developed to synthesize this important pharmacophore. Initially, Ru-catalyzed asymmetric hydrogenation of fluoride-substituted enamide 8 enabled the synthesis of sufficient quantities of compound 1 to support early preclinical studies. Subsequently, a novel, cost-effective route to this intermediate was developed utilizing a dynamic kinetic asymmetric transamination of ketone 9. This synthesis also features a robust Ullmann coupling to install a bis-aryl ether using a soluble Cu(I) catalyst. Finally, an enzymatic desymmetrization of meso-diester 7 was exploited for the construction of the γ-lactam moiety in 1.

An Efficient Catalytic Amidation of Esters Promoted by N-Heterocyclic Carbenes

An efficient NHC-catalyzed amidation between esters and amines or hydrazines is described. This strategy was tolerant for a wide scope of substrates, affording a series of amides (or hydrazides) in good to excellent yields (60-96%) under simple conditions. The approach was also used to synthesize the pharmaceutically relevant antidepressant moclobemide in 85% yield.

Synthesis and pharmacological evaluation of donepezil-based agents as new cholinesterase/monoamine oxidase inhibitors for the potential application against Alzheimer’s disease

In a continuing effort to develop multitargeted compounds as potential treatment agents against Alzheimer's disease (AD), a series of donepezil-like compounds were designed, synthesized and evaluated. In vitro studies showed that most of the designed compounds displayed potent inhibitory activities toward AChE, BuChE, MAO-B and MAO-A. Among them, w18 was a promising agent with balanced activities, which exhibited a moderate cholinesterase inhibition (IC50, 0.220 μM for eeAChE; 1.23 μM for eqBuChE; 0.454 μM for hAChE) and an acceptable inhibitory activity against monoamine oxidases (IC50, 3.14 μM for MAO-B; 13.4 μM for MAO-A). Moreover, w18 could also be a metal-chelator, and able to cross the blood–brain barrier with low cell toxicity on PC12 cells. Taken together, these results suggested that w18 might be a promising multitargeted compound for AD treatment.

4-Aminopiperidine derivatives as a new class of potent cognition enhancing drugs

Extrusion of one of the nitrogens of the piperazine ring of potent nootropic drugs previously described gave 4-aminopiperidine analogues that maintained high cognition enhancing activity in the mouse passive avoidance test. One of the new compounds (9, active at 0.01 mg/kg ip) may represent a new lead for the development of cognition enhancers useful to treat the cognitive deficit produced by neurodegenerative pathologies like Alzheimer's disease.

5-(heterocyclic alkyl)-6-aryl-dihydropyrimidines

This invention is directed to dihydropyrimidine compounds of the following formula: which are selective antagonists for human α1Areceptors. This invention is also related to uses of these compounds for lowering intraocular pressure, inhibiting cholesterol synthesis, relaxing lower urinary tract tissue, the treatment of benign prostatic hyperplasia, impotency, cardiac arrhythmia and for the treatment of any disease where antagonism of the α1Areceptor may be useful. The invention further provides a pharmaceutical composition comprising a therapeutically effective amount of the above-defined compounds and a pharmaceutically acceptable carrier.

2-alkylidene hydroxycumaranone derivatives

Compounds of the formula wherein R,R′, A,B,T and x have the meaning given in the specification possess uPA (urokinase-type plasminogen activator) antagonist activity and can be employed as antitumor and/or antimetastatic agents.

Microwave-assisted solvent-free parallel synthesis of thioamides

Rapid parallel synthesis of thioamides is described. A library of amides, synthesised by mixing acyl chlorides and diamines, was transformed into the corresponding thioamides utilising Lawesson's reagent as the oxygen/sulphur exchange reagent. Purification by solid-phase extraction afforded the library members in adequate purities and yields. (C) 2000 Elsevier Science Ltd.

4-N-linked-heterocyclic piperidine derivatives with high affinity and selectivity for human dopamine D4 receptors

The syntheses of a number of different N-linked heterocyclic pyrazole replacements based on the structure 1 are described (compounds 3-12) as hD4 ligands. After further optimisation the best compound identified was 13 which has high affinity for hD4 (5.2 nM) and >300-fold selectivity for hD4 receptors over hD2 and hD3 receptors.

Desulfonylation of Amides Using Samarium Iodide

The desulfonylation of N-sulfonyl amides can be achieved in reasonable to excellent yield by reaction with samarium(II) iodide (SmI2) in THF at room temperature. Deprotection of acyclic and cyclic amides bearing aryl and alkylsulfonyl groups is possible.

N-benzylpiperidine amides

N-benzylpiperidine amides, which have activity as Class III antiarrhythmic agents, acting by prolonging cardiac action potential repolarization. The invention further provides for compositions incorporating the compounds and methods of their use, as well as providing for pharmaceutically acceptable salts of the compounds.