130927-83-2

Basic information

• Product Name: 1-Benzyl-4-piperidine aceticacid
• Synonyms: 1-Benzyl-4-piperidine aceticacid;(1-benzylpiperidin-4-yl)acetic acid(SALTDATA: HCl)
• CAS NO: 130927-83-2
• Molecular Formula: C₁₄H₁₉NO₂
• Molecular Weight: 233.30616
• Product Categories: pharmacetical
• Mol File: 130927-83-2.mol

Chemical Properties

• Boiling Point: 378°Cat760mmHg
• Flash Point: 182.4°C
• Appearance: /
• Density: 1.121g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 4.49±0.10(Predicted)
• CAS DataBase Reference: 1-Benzyl-4-piperidine aceticacid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzyl-4-piperidine aceticacid(130927-83-2)
• EPA Substance Registry System: 1-Benzyl-4-piperidine aceticacid(130927-83-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 130927-83-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
1-Benzyl-4-piperidine acetic acid is used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals due to its potential biological activity, contributing to the development of new drugs and agricultural products.
Used in Neuroscience Research:
In the field of neuroscience, 1-Benzyl-4-piperidine acetic acid is utilized for research purposes, particularly in the study of the central nervous system. It aids in the development of new drugs for the treatment of various neurological disorders, enhancing our understanding of the brain and nervous system functions.
Used as an Analgesic and Anti-Inflammatory Agent:
1-Benzyl-4-piperidine acetic acid has been investigated for its potential as an analgesic and anti-inflammatory agent, offering a promising avenue for the development of new pain relief and anti-inflammatory medications.
Used in Polymer Production:
Additionally, 1-Benzyl-4-piperidine acetic acid has applications in the production of certain types of polymers, contributing to the advancement of materials science and the creation of innovative polymeric materials with diverse applications.

InChI:InChI=1/C14H19NO2/c16-14(17)10-12-6-8-15(9-7-12)11-13-4-2-1-3-5-13/h1-5,12H,6-11H2,(H,16,17)

Upstream product

• 71879-59-9 ethyl (1-benzylpiperidin-4-yl)acetate 
• 78056-67-4 1-(phenylmethyl)-4-piperidineacetonitrile 
• 120014-06-4 donepezil 
• 100-39-0 benzyl bromide 
• 100-52-7 benzaldehyde 
• 54401-85-3 pyridin-4-yl-acetic acid ethyl ester 
• 59184-90-6 ethyl (piperidin-4-yl)acetate 

Downstream Products

• 211631-82-2 2-(1-Benzyl-piperidin-4-yl)-N-[bis-(4-fluoro-phenyl)-methyl]-acetamide 
• 333364-03-7 4-[2-((diphenylmethyl)amino)ethyl]-1-(phenylmethyl)piperidine 
• 364385-38-6 2-[(1-benzyl-4-piperidinyl)methyl]-6-bromooxazolo[4,5-b]pyridine 

Relevant articles and documents

Synthesis and in vivo evaluation of 3-[11C]methyl-(3-methoxy-naphthalen)-2-yl-(1-benzyl-piperidin)-4-yl-acetate (SB-235753), as a putative dopamine D4 receptors antagonist for PET

(3-Methoxy-naphthalen)-2-yl-(1-benzyl-piperidin)-4-yl-acetate (SB-235753) was labelled with 11C (t(1/2) = 20.4 min) as a putative radioligand for the non-invasive assessment of Dopamine D4 receptors in vivo with positron emission tomography (PET). The precursor for the radiosynthesis 3-hydroxynaphthyl-2-[(N-benzyl)-piperidyl]-acetate hydrochloride was prepared by a four-step synthesis starting from ethyl-4-pyridyl acetate. The radiolabelling consisted of methylation with [11C]methyltriflate in dimethylformamide in the presence of potassium hydroxide. [11C]SB-235753, was synthesised in 30 min with a radiochemical yield of 10 ± 5% (EOS, non-decay corrected) with 99% radiochemical purity and specific radioactivity of 10 ± 3 Ci/μmol. Biodistribution studies in rats with [11C]SB-235753 showed the uniform distribution of the tracer within different areas of the murine brain. At 30 min after injection 99% of the radioligand in plasma and 100% in cerebellum was metabolised. These findings suggest that [11C]SB-235753 can not be a suitable tracer for dopamine D4 receptor studies with PET.

Donepezil oxidation: complementary chemical and spectroscopic exploration of products, mechanism and kinetics

Oxidation is a vital step of drug metabolism and hence a pharmaceutically relevant process. This study explores the potential of Donepezil, a widely used drug against mild to moderately severe Alzheimer's disease, to undergo oxidation using a mild, versatile oxidant Chloramine-T in acidic medium. A first-order dependency of rate on Donepezil and oxidant, fractional-order dependency on acid medium, independency of the rate on ionic concentration and an elevation of rate with increasing dielectric constant are revealed by the kinetic studies. The stoichiometry, thermodynamic properties, rate equation, mechanistic details are outlined, and identification of reaction products is supported by consistent oxidative degradation related UV, IR, 1H NMR and mass spectroscopic data. The spectroscopic results are in good agreement with theoretical predictions, providing an insight and deepen the understanding of oxidative metabolic pathway of Donepezil.

Synthesis and evaluation of multi-target-directed ligands for the treatment of Alzheimer's disease based on the fusion of donepezil and melatonin

A novel series of compounds obtained by fusing the acetylcholinesterase (AChE) inhibitor donepezil and the antioxidant melatonin were designed as multi-target-directed ligands for the treatment of Alzheimer's disease (AD). In vitro assay indicated that most of the target compounds exhibited a significant ability to inhibit acetylcholinesterase (eeAChE and hAChE), butyrylcholinesterase (eqBuChE and hBuChE), and β-amyloid (Aβ) aggregation, and to act as potential antioxidants and biometal chelators. Especially, 4u displayed a good inhibition of AChE (IC50value of 193?nM for eeAChE and 273?nM for hAChE), strong inhibition of BuChE (IC50value of 73?nM for eqBuChE and 56?nM for hBuChE), moderate inhibition of Aβ aggregation (56.3% at 20?μM) and good antioxidant activity (3.28?trolox equivalent by ORAC assay). Molecular modeling studies in combination with kinetic analysis revealed that 4u was a mixed-type inhibitor, binding simultaneously to catalytic anionic site (CAS) and the peripheral anionic site (PAS) of AChE. In addition, 4u could chelate metal ions, reduce PC12 cells death induced by oxidative stress and penetrate the blood–brain barrier (BBB). Taken together, these results strongly indicated the hybridization approach is an efficient strategy to identify novel scaffolds with desired bioactivities, and further optimization of 4u may be helpful to develop more potent lead compound for AD treatment.

Design, synthesis, and structure-activity relationships of a series of 3-[2-(1-benzylpiperidin-4-yl)ethylamino]pyridazine derivatives as acetylcholinesterase inhibitors

Starting from the 3-[2-(1-benzylpiperidin-4-yl)ethylamino]-6-phenylpyridazine 1, we performed the design, the synthesis, and the structure-activity relationships of a series of pyridazine analogues acting as AChE inhibitors. Structural modifications were achieved on four different parts of compound 1 and led to the following observations: (i) introduction of a lipophilic environment in the C-5 position of the pyridazine ring is favorable for the AChE-inhibitory activity and the AChE/BuChE selectivity; (ii) substitution and various replacements of the C-6 phenyl group are possible and led to equivalent or slightly more active derivatives; (iii) isosteric replacements or modifications of the benzylpiperidine moiety are detrimental to the activity. Among all derivatives prepared, the indenopyridazine derivative 4g was found to be the more potent inhibitor with an IC50 of 10 nM on electric eel AChE. Compared to compound 1, this represents a 12-fold increase in potency. Moreover, 3-[2-(1-benzylpiperidin-4-yl)ethylamino]-5-methyl-6-phenylpyridazine 4c, which showed an IC50 of 21 nM, is 100-times more selective for human AChE (human BuChE/AChE ratio of 24) than the reference compound tacrine.

Structure - Activity relationship studies of 4-[2-(diphenylmethoxy)ethyl]-1-benzylpiperidine derivatives and their N-analogues: Evaluation of behavioral activity of O- and N-analogues and their binding to monoamine transporters

In our effort to develop a pharmacotherapy for the treatment of cocaine addiction, we embarked on synthesizing novel molecules targeting the dopamine transporter (DAT) molecule in the brain as DAT has been implicated strongly in the reinforcing effect of

Tolerance in the replacement of the benzhydrylic O atom in 4-[2- (diphenylmethoxy)ethyl]-1-benzylpiperidine derivatives by an N atom: Development of new-generation potent and selective N-analogue molecules for the dopamine transporter

The replacement of the benzhydrylic oxygen atom of our previously developed dopamine transporter (DAT)-specific ligands 4-[2- (diphenylmethoxy)ethyl]-1-[(4-fluorophenyl)methyl]piperidine, 1a, and 4-[2- (bis(4-fluorophenyl)methoxy)ethyl]-1-benzylpiperidine