13603-25-3

Usage

Uses

Used in Pharmaceutical Industry:
3-Benzylpiperidine is used as a reagent for the preparation of Ketanserin analogues. These analogues are assessed for their structure-affinity relationships for 5-HT2 and 5-HT1C serotonin receptor binding. This application is significant in the development of new drugs targeting serotonin receptors, which play a crucial role in various neurological and psychiatric disorders.

InChI:InChI=1/C12H17N/c1-2-5-11(6-3-1)9-12-7-4-8-13-10-12/h1-3,5-6,12-13H,4,7-10H2/p+1/t12-/m1/s1

Upstream product

• 5424-19-1 3-Benzoylpyridine 
• 81976-72-9 3-phenylmethyl-2-piperidinone 
• 71-41-0 pentan-1-ol 
• 110-86-1 pyridine 
• 620-05-3 iodomethylbenzene 
• 1119-51-3 bromopentene 
• 84199-56-4 2-bromo-α-phenyl-3-pyridinemethanol 
• 100-44-7 benzyl chloride 
• 136421-73-3 1,3-dibenzyl piperidine 
• 865853-26-5 3-benzyl-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 620-95-1 3-benzylpyridine 

Downstream Products

• 1026916-01-7 3-benzyl-1-(2,2-dimethyl-2H-chromene-6-sulfonyl)-piperidine 
• 1053622-53-9 (3S,4R)-4-Amino-6-(3-benzyl-piperidine-1-sulfonyl)-2,2-dimethyl-chroman-3-ol 
• 1026490-94-7 3-benzyl-1-(2,2-dimethyl-1a,7b-dihydro-2H-1,3-dioxa-cyclopropa[a]naphthalene-6-sulfonyl)-piperidine 
• 1308375-81-6 3-((R)-2-amino-2-phenyl-ethyl)-5-(3-benzyl-piperidin-1-yl)-1-(2,6-difluoro-benzyl)-6-methyl-1H-pyrimidine-2,4-dione 
• 1602922-62-2 (4-chlorophenyl)-carbamic acid (S)-1-((S)-3-benzylpiperidin-1-ylmethyl)-2,2,2-trifluoro-ethyl ester p-toluenesulfonate 
• 1602922-61-1 (4-chlorophenyl)-carbamic acid (S)-1-((S)-3-benzylpiperidin-1-ylmethyl)-2,2,2-trifluoro-ethyl ester 
• 1602922-64-4 (4-chlorophenyl)-carbamic acid (S)-1-((R)-3-benzylpiperidin-1-ylmethyl)-2,2,2-trifluoro-ethyl ester 

Relevant academic research and scientific papers

Probing the proposed phenyl-A region of the sigma-1 receptor.

The proposed phenyl-A region of sigma (sigma) receptors accommodates several structural features. In this study we explored the possibility that appropriate structural features located at the phenyl-A region of sigma receptor sites could lead to more potent and selective agents for the sigma receptor subtypes. By keeping the phenyl-B substituent as the optimum omega-phenylpentyl moiety, and varying substituents in the phenyl-A region, we have observed changes in binding potency and selectivity at the sigma receptor subtypes. SAR for the binding of these compounds at sigma-2 sites was also examined.

Construction of azacycles by intramolecular amination of organoboronates and organobis(boronates)

Intramolecular amination of organoboronates occurs with a 1,2-metalate shift of an aminoboron ate complex to form azetidines, pyrrolidines, and piperidines. Bis(boronates) undergo site-selective amination to form boronate-containing azacycles. Enantiomerically enriched azacycles are formed with high stereospecificity.

An approach to the synthesis of 3-substituted piperidines bearing partially fluorinated alkyl groups

An approach to the synthesis of 3-substituted piperidines bearing partially fluorinated alkyl groups was proposed. The method was based on the DAST-mediated nucleophilic fluorination of easily available 2-bromopyridin-3-yl alcohols and ketones affording 2-bromo-3-(1-fluoroalkyl)pyridines and 2-bromo-3-(1,1-difluoroalkyl)pyridines, respectively, followed by catalytic hydrogenation. The hydrogenation step was studied with common heterogeneous Pd-, Pt-, and Rh-based catalyst. It was found that in the case of fluoroalkyl derivatives, the pyridine core reduction was accompanied by hydrodefluorination, which became a limitation of the strategy. Nevertheless, the method worked well with 1,1-difluoroalkyl derivatives

B(C6F5)3-Catalyzed Cascade Reduction of Pyridines

B(C6F5)3 has been found to be an effective catalyst for reduction of pyridines and other electron-deficient N-heteroarenes with hydrosilanes (or hydroboranes) and amines as the reducing reagents. The success of this development hinges upon the realization of a cascade process of dearomative hydrosilylation (or hydroboration) and transfer hydrogenation. The broad functional-group tolerance (e.g. ketone, ester, unactivated olefins, nitro, nitrile, heterocycles, etc.) implies high practical utility.

Approach to 3-(Cyclo)alkylpiperidines through 'sp3-sp3 via sp2-sp3' Coupling

The idea of introducing (cyclo)alkyl substituents at the C-3 atom of the piperidine ring, that is, formal sp3-sp3 retrosynthetic disconnection, is implemented through a two-step reaction sequence including directed ortho metalation of a pyridine derivative and the subsequent quenching with a carbonyl compound, followed by catalytic hydrogenation. This robust but very efficient method allows for multigram preparation of sp3-rich 3-(cyclo)alkylpiperidines, which are valuable building blocks for medicinal chemistry and other areas.

HETEROCYCLIC COMPOUNDS AND METHODS FOR THEIR USE

The present invention relates to heterocyclic compounds useful for antagonising angiotensin II Type 2 (AT2) receptor. More particularly the invention relates to pyrrolidine and azetidine compounds, compositions containing them and their use in methods of treating or preventing disorders or diseases associated with AT2 receptor function including neuropathic pain, inflammatory pain, conditions associated with neuronal hypersensitivity, impaired nerve conduction velocity, cell proliferation disorders, disorders associated with an imbalance between bone resorption and bone formation and disorders associated with aberrant nerve regeneration.

Improved synthesis of quinine alkaloids with the Teoc protective group

TeocCl (Teoc: C(O)O(CH2)2TMS) generated in situ was conveniently used for trans-protection of the N-Bn piperidine intermediate to N-Teoc piperidine. Later, deprotection of the Teoc group and the subsequent quinuclidine ring formation was achieved with CsF in a domino fashion to afford the quinine alkaloids.

Piperidine derivatives

The invention provides piperidine derivatives of the general formula STR1 or an acid-addition salt or metal salt complex thereof, in which R represents a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, aryl, arylcarbonyl, heterocyclyl or heterocyclyloxy group; R1 represents an optionally substituted alkyl, phenyl, benzyl or cycloalkyl group; R2 represents a hydrogen atom or an optionally substituted alkyl group; one of W and X represents --CH2 --, --CH2 CH2 -- or --O--, the other of W and X being --CH2 -- or --CH2 CH2 or X represents a single chemical bond; m is 0 or 1 and n represents an integer from 0 to 3; processes for their preparation; compositions containing such compounds and their use as fungicides.

4-[[3-[α-Aminobenzyl]phenyl]methyl]morpholine and 4-[-[3-benzoylphenyl]ethyl]morpholine

N-{2, 3- and 4-[R1 -(phenyl)-C(=X)]-phenyl-lower-alkyl}amines, useful as anti-inflammatory agents, are prepared either by reduction of 2-, 3- or 4-[R1 -(phenyl)-CO]-phenyl-lower-alkanoylamines, which are also useful as anti-inflammatory agents; by benzoylating a phenyl-lower-alkylamine; by reaction of a 2-, 3- or 4-lithiophenyl-lower-alkylamine with a R1 -(phenyl)-carboxaldehyde, a R1 -(phenyl)-lower-alkyl ketone or a R1 -(phenyl)-carbonitrile; by reaction of a 2-, 3- or 4-[R1 -(phenyl)-CO]-phenyl-lower-alkyl tosylate with an appropriate amine; or by transformations involving manipulations of a carbonyl or carbinol group.

Intermediates for preparing anti-inflammatory phenyl-lower-alkylamines

N-{3- and 4-[R1 -(phenyl)-C(=X)]-phenyl-lower-alkyl}amines, useful as anti-inflammatory agents, are prepared either by reduction of 3- or 4-[R1 -(phenyl)-CO]-phenyl-lower-alkanoylamines, which are also useful as anti-inflammatory agents; by benzoylating a phenyl-lower-alkylamine; by reaction of a 3- or 4-lithiophenyl-lower-alkylamine with a R1 -(phenyl)-carboxaldehyde, a R1 -(phenyl)-lower-alkyl ketone or a R1 -(phenyl)-carbonitrile or by transformations involving manipulations of a carbonyl or carbinol group.