62718-31-4

Usage

Uses

Used in Pharmaceutical Synthesis:
1-Benzylpiperidine-4-carbonitrile is utilized as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications.
Used in Medicinal Chemistry Research:
In the realm of medicinal chemistry, 1-Benzylpiperidine-4-carbonitrile is employed as a compound of interest for exploring its biological activities, which may lead to the discovery of novel therapeutic agents.
Used in Organic Chemistry:
As a versatile building block, 1-Benzylpiperidine-4-carbonitrile is used in organic chemistry for the synthesis of various organic compounds, contributing to the advancement of chemical libraries and the creation of new chemical entities with potential applications in different industries.

InChI:InChI=1/C13H16N2/c14-10-12-6-8-15(9-7-12)11-13-4-2-1-3-5-13/h1-5,12H,6-9,11H2

Upstream product

• 62992-68-1 1-benzyl-piperidine-4-carboxylic acid amide 
• 1071043-38-3 Phosphoric acid 1-benzyl-4-cyano-piperidin-4-yl ester diethyl ester 
• 4395-98-6 4-cyanopiperidine 
• 100-39-0 benzyl bromide 
• 3612-20-2 1-phenylmethyl-4-piperidone 
• 2942-58-7 diethyl cyanophosphonate 
• 137076-22-3 tert butyl 4-formylpiperidine-1-carboxylate 
• 88796-02-5 1-benzylpiperidine-4-carbaldehyde oxime 
• 190446-85-6 tert-butyl 4-((hydroxyimino)methyl)piperidine-1-carboxylate 
• 10315-06-7 1-benzylpiperidine-4-carboxylic acid methyl ester 
• 7462-86-4 methyl piperidine-4-carboxylate hydrochloride 
• 498-94-2 isonipecotic acid 
• 10315-07-8 N-benzylpiperidine-4-carboxylic acid 

Downstream Products

• 88796-05-8 1-(1-Benzyl-piperidin-4-yl)-propan-1-one 
• 88796-07-0 1-(1-Benzyl-piperidin-4-yl)-pentan-1-one 
• 86542-84-9 (1-benzylpiperidin-4-yl)(cyclopentyl)methanone 
• 76315-69-0 [1-(phenylmethyl)-4-piperidinyl] (thien-2-yl)-methanone 
• 86542-94-1 1-(piperidine-4-yl)-propan-1-one 
• 86542-97-4 Cyclohexyl-piperidin-4-yl-methanone 
• 86543-30-8 N-(2-Cyano-4,5-dimethoxy-phenyl)-4-(1-hydroxy-pentyl)-piperidine-1-carboximidothioic acid methyl ester 
• 80030-66-6 N-(2-Cyano-4,5-dimethoxy-phenyl)-4-propionyl-piperidine-1-carboximidothioic acid methyl ester 
• 86543-23-9 4-(1-Hydroxy-pentyl)-piperidine-1-carbothioic acid (2-cyano-4,5-dimethoxy-phenyl)-amide 
• 86543-17-1 4-Propionyl-piperidine-1-carbothioic acid (2-cyano-4,5-dimethoxy-phenyl)-amide 
• 80030-67-7 N-(2-Cyano-4,5-dimethoxy-phenyl)-4-pentanoyl-piperidine-1-carboximidothioic acid methyl ester 
• 86543-31-9 N-(2-Cyano-4,5-dimethoxy-phenyl)-4-(cyclopentyl-hydroxy-methyl)-piperidine-1-carboximidothioic acid methyl ester 
• 86543-24-0 4-(Cyclopentyl-hydroxy-methyl)-piperidine-1-carbothioic acid (2-cyano-4,5-dimethoxy-phenyl)-amide 
• 86543-18-2 4-Pentanoyl-piperidine-1-carbothioic acid (2-cyano-4,5-dimethoxy-phenyl)-amide 

Relevant academic research and scientific papers

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.

Preparation of Indolenines via Nucleophilic Aromatic Substitution

An unusual aromatic substitution to access indolenines is described. 2-(2-Methoxyphenyl)acetonitrile derivatives are reacted with various alkyl and aryl Li reagents to furnish the corresponding indolenine products, constituents of natural products, and cyanine dyes such as indocyanine green. This new method was used to synthesize 41 indolenines with large functional group tolerance, and selected examples were further converted to the corresponding indolenine dyes. Key experiments provide insight into the mechanism of this nucleophilic aromatic substitution.

Copper-Catalyzed Alkylation of Nitroalkanes with α-Bromonitriles: Synthesis of β-Cyanonitroalkanes

Copper catalysis now enables the efficient C-alkylation of nitroalkanes with α-bromonitriles. Using a simple and inexpensive catalyst, this process provides access to β-cyanonitroalkanes. The method is highly tolerant of various functional groups and substitution patterns. These functionally dense products serve as orthogonally masked 1,3-diamines, which can be revealed selectively for access to differentially substituted diamines. These products can also be exploited for the formation of complex cyanoalkenes and 5-aminoisoxazoles.

Synthesis of Nitriles from Aldoximes and Primary Amides Using XtalFluor-E

The dehydration reaction of aldoximes and amides for the synthesis of nitriles using [Et2NSF2]BF4 (XtalFluor-E) is described. Overall, the reaction proceeds rapidly (normally 1 h) at room temperature in an environmentally benign solvent (EtOAc) with only a slight excess of the dehydrating agent (1.1 equiv). A broad scope of nitriles can be prepared, including chiral nonracemic ones. In addition, in a number of cases, further purification of the nitrile after the workup was not required.

Synthesis of the pleuromutilin antibiotic SB-268091: A new practical and efficient synthesis of quinuclidine-4-thiol

A synthesis of the pleuromutilin antibiotic SB-268091 is described which includes a new and improved route to the quinuclidine-4-thiol ligand. This chemistry has been run on multikilo scale and involved a reductive double debenzylation using sodium in liquid ammonia. Alternative conditions have been developed to prepare quinuclidine-4-thiol which avoid the use of sodium in liquid ammonia. The generality of this process to prepare differentially S-protected quinuclidine-4-thiols is also discussed and exemplified by the preparation of a range of analogues.

Heteroatom-directed alkylcyanation of alkynes

Alkanenitriles having a heteroatom such as nitrogen, oxygen, and sulfur at the γ-position are found to add across alkynes stereo-and regioselectively by nickel/Lewis acid catalysis to give highly substituted acrylonitriles. The heteroatom functionalities likely coordinate to the nickel center to make oxidative addition of the C-CN bonds of the alkyl cyanides kinetically favorable, forming a five-membered nickelacycle intermediate and, thus, preventing β-hydride elimination to allow the alkylcyanation reaction.

OCTAHYDROPYRROLO [3, 4-C] PYRROLE DERIVATIVES AN THEIR USE AS ANTIVIRAL AGENTS

Chemokine receptor antagonists, in particular, 3,7-diazabicyclo [3.3.0] octane compounds according to formula (I) wherein R1-R3 and Ar are as defined herein are antagonists of chemokine CCR5 receptors which are useful for treating or preventing an human immunodeficiency virus (HIV) infection, or treating AIDS or ARC. The invention further provides methods for treating diseases that are alleviated with CCR5 antagonists. The invention includes pharmaceutical compositions and methods of using the compounds for the treatment of these diseases. The invention further includes processes for the preparation of compounds according to formula (I).

5-HTX MODULATORS

This invention relates to compounds which bind to serotonin receptors inside or outside the central nervous system, in particular compounds which bind to the 5-HT2 or 5-HT7 receptors, their preparation and use, compositions containing them, and methods of treatment using them.

MODULATORS OF PERIPHERAL 5-HT RECEPTORS

Novel modulators of 5-HT4 receptors have been developed which have a selectivity for peripheral receptors rather than those of the central nervous systems. Theses include novel derivatives of known modulators as well as entirely novel entities. Surprisingly, the derivatised compounds of the known modulators maintain a high binding affinity to 5-HT4 receptors, despite the presence of an acidic moiety at the end of an optional chain. The entirely novel entities also exhibit good binding affinity to 5-HT4 receptors. All of the compounds of the invention have a common motif which includes a basic nitrogen moiety and an acidic moiety. The compounds of the invention, due at least in part to their high ionisation potential at physiological pH, have the unique properties of selectively for peripheral 5HT4 receptors over those of the CNS, good binding affinity, and selectively of 5HT4 receptors over other serotonin receptors.

SUBSTITUTED 3- AND 4- AMINOMETHYLPIPERIDINES FOR USE AS BETA-SECRETASE IN THE TREATMENT OF ALZHEIMER’S DISEASE

The invention relates to novel compounds, which are substituted chiral or achiral derivatives of 3- or 4- aminomethylpiperidine of the general formula (I). The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more compounds of general formula (I) and especially their use as inhibitors of beta-secretases for the treatment of Alzheimer’s disease.