10315-07-8

Basic information

• Product Name: 1-BENZYLPIPERIDINE-4-CARBOXYLIC ACID
• Synonyms: BUTTPARK 33\04-90;1-BENZYL-ISONIPECOTIC ACID;1-BENZYLPIPERIDINE-4-CARBOXYLIC ACID;1-BENZYL-4-PIPERIDINE CARBOXYLIC ACID;N-BENZYL-ISONIPECOTIC ACID;1-(phenylmethyl)-4-Piperidinecarboxylic acid;N-Benzylpiperidine-4-carboxylic acid;1-benzylpiperidin-4-carboxylic acid
• CAS NO: 10315-07-8
• Molecular Formula: C₁₃H₁₇NO₂
• Molecular Weight: 219.28
• Product Categories: pharmacetical;Carboxylic Acids;Pyrans, Piperidines &Piperazines;Carboxylic Acids;Pyrans, Piperidines & Piperazines
• Mol File: 10315-07-8.mol

Chemical Properties

• Melting Point: 169.0-170.5 °C
• Boiling Point: 358.584 °C at 760 mmHg
• Flash Point: 170.666 °C
• Appearance: /
• Density: 1.165
• Vapor Pressure: 9.13E-06mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: 2-8°C
• PKA: 4.02±0.20(Predicted)
• CAS DataBase Reference: 1-BENZYLPIPERIDINE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZYLPIPERIDINE-4-CARBOXYLIC ACID(10315-07-8)
• EPA Substance Registry System: 1-BENZYLPIPERIDINE-4-CARBOXYLIC ACID(10315-07-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• Hazardous Substances Data: 10315-07-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-BENZYLPIPERIDINE-4-CARBOXYLIC ACID is used as a precursor in the synthesis of various drugs for the treatment of central nervous system disorders and neuropsychiatric conditions. Its unique structure allows it to be a key component in the development of medications that address these complex health issues.
Used in Drug Discovery and Development:
1-BENZYLPIPERIDINE-4-CARBOXYLIC ACID is utilized as a building block in the preparation of other organic compounds, contributing to the advancement of new drug candidates and the enhancement of existing pharmaceutical formulations.
Used in Academic and Industrial Research:
1-BENZYLPIPERIDINE-4-CARBOXYLIC ACID is employed as a valuable chemical in research settings, facilitating the exploration of new chemical pathways and the understanding of its interactions with biological systems, thereby supporting the innovation of novel therapeutic approaches.

InChI:InChI=1/C13H17NO2/c15-13(16)12-6-8-14(9-7-12)10-11-4-2-1-3-5-11/h1-5,12H,6-10H2,(H,15,16)

Upstream product

• 498-94-2 isonipecotic acid 
• 7462-86-4 methyl piperidine-4-carboxylate hydrochloride 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 10315-06-7 1-benzylpiperidine-4-carboxylic acid methyl ester 
• 2971-79-1 isonipecotic acid methyl ester 
• 66-99-9 β-naphthaldehyde 
• 123-91-1 1,4-dioxane 
• 24228-40-8 N-benzyl isonipecotic acid ethyl ester 
• 1126-09-6 4-carbethoxypiperidine 

Downstream Products

• 914226-80-5 1-benzyl-N-isopropylpiperidine-4-carboxamide 
• 22065-85-6 N-benzyl-4-formylpiperidine 
• 88915-26-8 4-aminomethyl-1-benzylpiperidine 
• 1159687-96-3 C₂₁H₃₄N₂O₄ 
• 69082-42-4 N-(5-chloro-2-methoxy-4-nitrophenyl)-1-(phenylmethyl)-4-piperidinecarboxamide 
• 69082-47-9 N-(4-amino-5-chloro-2-methoxyphenyl)-1-(phenylmethyl)-4-piperidinecarboxamide 
• 195503-44-7 1-benzyl-N-methyl-N-phenylpiperidine-4-carboxamide 
• 195503-48-1 (6-Benzyl-1,6-diaza-spiro[2.5]oct-1-en-2-yl)-methyl-phenyl-amine 
• 867060-16-0 (1-benzyl-piperidin-4-ylmethyl)-pentadecyl-amine 
• 1013330-23-8 (1-benzylpiperidin-4-yl)(4-tert-butylpiperazin-1-yl)methanone 
• 259653-65-1 1-benzyl-piperidine-4-carboxylic acid (2,6-dimethoxy-5-methyl-5,6,7,8-tetrahydro-quinolin-5-yl)-amide 
• 108297-01-4 1-benzylpiperidine-4-carbonyl chloride 

Relevant articles and documents

Novel N-benzylpiperidine carboxamide derivatives as potential cholinesterase inhibitors for the treatment of Alzheimer's disease

A series of fifteen acetylcholinesterase inhibitors were designed and synthesised based upon the previously identified lead compound 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl 1-benzylpiperidine-4-carboxylate (5) which showed good inhibitory activity (IC50 0.03 ± 0.07 μM) against acetylcholinesterase. A series of compounds were prepared wherein the ester linker in the original lead compound was exchanged for a more metabolically stable amide linker and the indanone moiety was exchanged for a range of aryl and aromatic heterocycles. The two most active analogues 1-benzyl-N-(5,6-dimethoxy-8H-indeno[1,2-d]thiazol-2-yl)piperidine-4-carboxamide (28) and 1-benzyl-N-(1-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl) piperidine-4-carboxamide (20) afforded in vitro IC50 values of 0.41 ± 1.25 and 5.94 ± 1.08 μM, respectively. In silico screening predicts that 20 will be a blood brain-barrier permeant, and molecular dynamic simulations are indicative of a close correlation between the binding of 20 and the Food and Drug Administration-approved cholinesterase inhibitor donepezil (1).

Synthesis method of N-benzyl-4-piperidine formaldehyde

The invention belongs to the technical field of medicine synthesis, and particularly relates to a synthesis method of N-benzyl-4-piperidine formaldehyde. According to the invention, 4-piperidinecarboxylic acid is used as a raw material; an esterification reaction is carried out to generate 4-methyl piperidinecarboxylate hydrochloride; an alkylation reaction is carried out on N-benzyl-4-methyl piperidinecarboxylate hydrochloride to generate N-benzyl-4-methyl piperidinecarboxylate; n-benzyl-4-methyl piperidinecarboxylate is hydrolyzed to obtain N-benzyl-4-piperidinecarboxylic acid, N-benzyl-4-piperidinecarboxylic acid is subjected to an acylation reaction to generate N-benzyl-4-piperidinecarboxamide, N-benzyl-4-piperidinecarboxamide is dehydrated to obtain 1-benzylpiperidine-4-nitrile, and 1-benzylpiperidine-4-nitrile is subjected to a reduction reaction to generate N-benzyl-4-piperidineformaldehyde. The method is mild in reaction condition, simple in aftertreatment and high in yield, N-benzyl-4-piperidinecarboxaldehyde can be obtained at the high yield at the temperature of 0 DEG C, column chromatography is not needed, and repeatability is high.

4,5-dimethoxy-2-nitrobenzohydrazides and 1-(1-benzylpiperidin-4-yl)ethan-1-ones as potential antioxidant/cholinergic endowed small molecule leads

The objective of this research is to generate leads for developing our ultimate poly-active molecules with utility in central nervous system (CNS) diseases. Indeed, poly-active molecules capable of mitigating brain free radical damage while enhancing acetylcholine signaling (via cholinesterase inhibition) are still being sought for combating Alzheimer’s disease (AD). We differentiate “poly-active” agents from “multi-target” ones by defining them as single molecular entities designed to target only specific contributory synergistic pharmacologies in a disease. For instance, in AD, free radicals either initiate or act in synergy with other pharmacologies, leading to disease worsening. For this preliminary report, a total of 14 (i.e., 4,5-dimethoxy-2-nitrobenzohydrazide plus 1-(1-benzylpiperidin-4-yl)ethan-1-one) derivatives were synthesized and screened, in silico and in vitro, for their ability to scavenge free radicals and inhibit acetylcholinesterase (AChE)/butyrylcholinesterase (BuChE) enzymes. Overall, six derivatives (4a, 4d, 4e, 4f, 4g, 9b) exhibited potent (>30%) antioxidant properties in the oxygen radical absorbance capacity (ORAC) assay. The antioxidant values were either comparable or more potent than the comparator molecules (ascorbic acid, resveratrol, and trolox). Only three compounds (4d, 9a, 9c) yielded modest AChE/BuChE inhibitions (>10%). Please note that a SciFinder substance data base search confirmed that most of the compounds reported herein are new, except 9a and 9c which are also commercially available.

Method for synthesizing N-benzyl-4-piperidinecarboxylate

The invention belongs to the technical field of pharmaceutical chemicals and in particular discloses a method for synthesizing N-benzyl-4-piperidinecarboxylate. The process comprises the following steps: by taking isonipecotic acid and benzyl chloride as raw materials and taking 1,2-dichloroethane as a solvent, heating and reacting, adding water to wash after cooling, drying the organic layer, filtering and concentrating, thereby obtaining the N-benzyl-4-piperidinecarboxylate. According to the synthetic method, the used solvent 1,2-dichloroethane is concentrated and collected and can be recycled, the method is environmentally friendly, and the cost of the raw materials is greatly reduced.

NOVEL GPR119 AGONIST COMPOUNDS

The present invention relates to novel compounds of formula (I), process for preparation of the same and composition comprising these compounds.

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.

2,4-Diamino-quinazolines as inhibitors of β-catenin/Tcf-4 pathway: Potential treatment for colorectal cancer

The synthesis and SAR of a series of 2,4-diamino-quinazoline derivatives as β-catenin/Tcf-4 inhibitors are described. This series was developed by modifying the initial lead 1, which was identified by screening of our compound library and found to inhibit

CHEMICAL COMPOUNDS

The present invention provides compounds of formula (I) wherein R1, R2, R3, R4, Het and m are as defined in the description. The compounds of the present invention are modulators, especially antagonists, of the

Design and synthesis of Rho kinase inhibitors (II)

In a previous study, we identified several structurally unrelated scaffolds of the Rho kinase inhibitor using pharmacophore information obtained from the results of a high-throughput screening and structural information from a homology model of Rho kinase. 1H-Indazole is one of the candidate scaffolds on which a new series of potent Rho kinase inhibitors could be developed. In this study, the detailed structure-activity relationship of 1H-indazole analogues was studied. During this study, we found that the cell-free enzyme inhibitory potential of Rho kinase inhibitors having the 1H-indazole scaffold did not necessarily correlate with their inhibitory potential toward the chemotaxis of cultured cells. The choice of the linker substructure was shown to be an important factor for the 1H-indazole analogues to inhibit the chemotaxis of cells. Optimization of the 1H-indazole inhibitors with respect to the in vitro inhibition of monocyte chemotaxis induced by MCP-1 was carried out. The inhibitory potential was improved both in the cell-free enzyme assay and in the chemotaxis assay.

BENZAMIDE DERIVATIVES

A compound represented by formula (1): wherein X is a single bond or a substituted or unsubstituted lower alkylene group; Z is a saturated or unsaturated monocyclic hydrocarbon ring group or the like; and each of R1, R2, R3 and R4, which may be the same or different, is a hydrogen atom, a halogen atom, a nitro group, a cyano group, a carboxyl group, a substituted or unsubstituted alkyl group, or the like, a prodrug of said compound, or a pharmaceutically acceptable salt of said compound or prodrug has inhibitory effect on Rho kinase and hence is useful for treating diseases which are such that morbidity due to them is expected to be improved by inhibition of Rho kinase and secondary effects such as inhibition of the Na+/H+ exchange transport system caused by the Rho kinase inhibition, for example, hypertension.