14813-01-5

Usage

Uses

Used in Pharmaceutical Industry:
1-Benzyl-3-piperidinol is used as a reactant for the bioresolution of tertiary amino ester protic ionic liquids using subtilisin. This application is significant in the development of novel pharmaceutical compounds with improved selectivity and efficacy.
1-Benzyl-3-piperidinol is also used as a reactant for the synthesis of muscarinic M3 selective antagonists. These antagonists are important in the treatment of various conditions, such as overactive bladder and chronic obstructive pulmonary disease (COPD), by selectively targeting the muscarinic M3 receptor.
In addition, 1-Benzyl-3-piperidinol is utilized as a reactant for the synthesis of Rho kinase inhibitors. These inhibitors play a crucial role in the treatment of various diseases, including cardiovascular and neurological disorders, by targeting the Rho kinase enzyme.
Furthermore, 1-Benzyl-3-piperidinol is used in the synthesis of piperidine derivatives for investigations into α-adrenoreceptor direct activation. These derivatives are essential in understanding the role of α-adrenoreceptors in various physiological processes and can potentially lead to the development of new treatments for conditions such as hypertension and erectile dysfunction.
Overall, 1-Benzyl-3-piperidinol is a versatile compound with a wide range of applications in the pharmaceutical industry, particularly in the development of novel drugs targeting specific receptors and enzymes. Its chemical properties and structural features make it an essential building block in the synthesis of various therapeutic agents.

InChI:InChI=1/C12H17NO/c14-12-7-4-8-13(10-12)9-11-5-2-1-3-6-11/h1-3,5-6,12,14H,4,7-10H2

Upstream product

• 3323-73-7 1-Benzyl-3-hydroxypyridinium chloride 
• 6859-99-0 3-hydroxypiperazine 
• 100-44-7 benzyl chloride 
• 50606-58-1 N-benzyl-3-piperidinone hydrochloride 
• 100-39-0 benzyl bromide 
• 109-00-2 3-HYDROXYPYRIDINE 
• 64051-79-2 piperidin-3-ol hydrochloride 
• 111492-68-3 3-hydroxy-1-benzyl-2-piperidinone 
• 62214-78-2 1-benzyl-3-hydroxypyridin-1-ium bromide 
• 100-52-7 benzaldehyde 
• 40114-49-6 1-benzyl-3-piperidone 

Downstream Products

• 91599-74-5 benidipine hydrochloride 
• 129262-07-3 (RS)-(SR)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 1-(phenylmethyl)-3-piperidinyl ester hydrochloride 
• 121138-42-9 N-benzyl-3-piperidinyl 2-cyanoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 40114-49-6 1-benzyl-3-piperidone 
• 85387-34-4 1-benzylpiperidin-3-yl acetoacetate 
• 170749-10-7 1-benzylpiperidine-3-yl cyanoacetate 
• 174621-91-1 rac-N-benzyl-3-piperidinyl acetate 
• 58879-07-5 1-benzyl-3-phenyl-3-piperidinol 
• 6859-99-0 3-hydroxypiperazine 
• 928782-46-1 1-benzyl-3-(4-nitrophenoxy)piperidine 
• 1200404-99-4 1-benzyl-3-piperidinyl butyrate butyric acid salt 
• 1227866-76-3 methanesulfonic acid (1-benzyl-piperidin-3-yl)methyl ester 
• 57734-44-8 1-benzyl-2-aminomethyl-pyrrolidine 
• 60169-68-8 2-azidomethyl-1-benzylpyrrolidine 

Relevant academic research and scientific papers

N-alkylpiperidine carbamates as potential anti-Alzheimer's agents

Compounds capable of interacting with single or multiple targets involved in Alzheimer's disease (AD) pathogenesis are potential anti-Alzheimer's agents. In our aim to develop new anti-Alzheimer's agents, a series of 36 new N-alkylpiperidine carbamates was designed, synthesized and evaluated for the inhibition of cholinesterases [acetylcholinesterase (AChE) and butyrylcholinesterase (BChE)] and monoamine oxidases [monoamine oxidase A (MAO-A and monoamine oxidase B (MAO-B)]. Four compounds are very promising: multiple AChE (IC50 = 7.31 μM), BChE (IC50 = 0.56 μM) and MAO-B (IC50 = 26.1 μM) inhibitor 10, dual AChE (IC50 = 2.25 μM) and BChE (IC50 = 0.81 μM) inhibitor 22, selective BChE (IC50 = 0.06 μM) inhibitor 13, and selective MAO-B (IC50 = 0.18 μM) inhibitor 16. Results of enzyme kinetics experiments showed that despite the carbamate group in the structure, compounds 10, 13, and 22 are reversible and non-time-dependent inhibitors of AChE and/or BChE. The resolved crystal structure of the complex of BChE with compound 13 confirmed the non-covalent mechanism of inhibition. Additionally, N-propargylpiperidine 16 is an irreversible and time-dependent inhibitor of MAO-B, while N-benzylpiperidine 10 is reversible. Additionally, compounds 10, 13, 16, and 22 should be able to cross the blood-brain barrier and are not cytotoxic to human neuronal-like SH-SY5Y and liver HepG2 cells. Finally, compounds 10 and 16 also prevent amyloid β1–42 (Aβ1–42)-induced neuronal cell death. The neuroprotective effects of compound 16 could be the result of its Aβ1–42 anti-aggregation effects.

Transition-Metal-Free Total Synthesis and Revision of the Absolute Configuration of Pipermethystine

Starting from 3-hydroxy piperidines, a novel transition-metal-free strategy to 5-hydroxy-5,6-dihydro-2(1H)pyridones is reported. This unprecedented approach, which provides a practical, economical, and ecofriendly alternative to either the classical ring-closing metathesis of N-homoallyl-unsaturated amides or the dehydrogenation of amides, occurs by means of a triple C-H functionalization of three unreactive piperidine sp3 carbons. The completion of the total synthesis revealed that the natural levo-isomer possesses the R absolute configuration, not S.

A benidipine hydrochloride method for synthesizing intermediate

The invention discloses a synthetic method for a benidipine hydrochloride intermediate. The synthetic method comprises performing a nucleophilic substitution reaction on 3-hydroxypyridine and a benzyl halide under a solvent refluxing condition, so as to generate 1-benzyl-3-hydroxypyridiniumhalide; taking an alcohol as a solvent and reducing 1-benzyl-3-hydroxypyridiniumhalide to generate 1-benzyl-3-piperidinol; then performing transesterification reaction on 1-benzyl-3-piperidinol and ethyl acetoacetate under a refluxing condition by taking toluene as a solvent in the presence/absence of a catalyst, and under the condition that less than 30% of the alcohol is left, performing normal-pressure distillation until the alcohol completely finishes reaction, so as to obtain the product. The synthetic method is simple and has the three-step total yield of 80% or more, and all employed materials are industrialized products and are cheap and easily obtained, and the quality is easily controlled.

Synthesis method of N-benzyl-3-hydroxypiperidine

The invention discloses a synthesis method of N-benzyl-3-hydroxypiperidine, and belongs to the technical field of organic synthesis. In the absence of alkaline, and after 3-hydroxypiperidine is protected by halogenated benzyl, hexamethyldisilane is added to continue the reaction to obtain N-benzyl-3-trimethylsiloxidine, and then alcohols solvent or fluorine-containing ionicsalt is added for deprotection to obtain high-purity N-benzyl-3-hydroxypiperidine. According to the synthesis method of N-benzyl-3-hydroxypiperidine, the raw materials and reagents are cheap and easy to obtain, the reactioncondition is mild, continuous operation can be conducted, the product purity reaches up to 99.5% or above, and the method is suitable for enlarged production on a large scale.

Stereo-complementary bioreduction of saturated N-heterocyclic ketones

The asymmetric bioreduction of several saturated N-heterocyclic ketones is demonstrated in a stereo-complementary fashion using the ketoreductases READH and ChKRED20 for the production of (S)- and (R)-alcohols, respectively. The reaction accepts substrates with a five-, six- or seven-membered ring, and exhibits excellent stereoselectivity when using 2-propanol as both the ultimate reducing agent and cosolvent, achieve >99% ee in the majority of cases for both enantiomers.

Efficient and chemoselective reduction of pyridines to tetrahydropyridines and piperidines via rhodium-catalyzed transfer hydrogenation

Promoted by iodide anion the rhodium complex dimer, [Cp RhCl 2]2, catalyzes efficiently the transfer hydrogenation of various quaternary pyridinium salts under mild conditions, affording not only piperidines but also 1,2,3,6-tetrahydropyridines in a highly chemoselective fashion, depending on the substitution pattern at the pyridinium ring. The reduction is conducted in azeotropic formic acid/triethylamine (HCOOH-Et 3N) mixture at 40 °C, with catalyst loadings as low as 0.005mol% being feasible. Copyright

PYRIDINE-3-CARBOXYAMIDE DERIVATIVE

To provide a novel JAK3 inhibitor that is useful as a preventive and/or therapeutic agent for rejection and graft versus host disease (GvHD) in organ transplantation, rheumatoid arthritis, multiple sclerosis, systemic lupus erythematosus, Sj?gren syndrome, Behcet's disease, type I diabetes mellitus, autoimmune thyroiditis, idiopathic thrombocytopenic purpura, ulcerative colitis, Crohn's disease, asthma, allergic rhinitis, atopic dermatitis, contact dermatitis, urticaria, eczema, psoriasis, allergic conjunctivitis, uveitis, cancer, leukemia and the like. The pyridine-3-carboxyamide derivative represented by the general formula (1): or its salt or a solvate thereof.

Enantioselective access to all-trans 5-alkylpiperidine-3,4-diols: Application to the asymmetric synthesis of the 1-n-iminosugar (+)-isofagomine

Access to 3,4-disubstituted N-benzylprolinol derivatives is described that, after optimization of the ring-enlargement reaction conditions, could be efficiently transformed into the corresponding 3-hydroxypiperidines. This approach was applied to the asym

QUINOLONE ANTIBACTERIAL AGENTS

Compounds of formula (I, II, III, IV, V, and VI) and methods for their preparation are disclosed. Further disclosed are methods of making biologically active compounds of formula (I) as well as pharmaceutically acceptable compositions comprising compounds of formula (I). Compounds of formula (I) as disclosed herein can be used in a variety of applications including use as antibacterial agents.

PENEM DERIVATIVES AND ANTIMICROBIAL AGENT CONTAINING THE SAME

A penem derivative represented by the following formula (I): wherein R1represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkenylthio group, a substituted or unsubstituted aralkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic thio group, a substituted or unsubstituted acylthio group, a mercapto group or a hydrogen atom, and R2represents a hydrogen atom or a carboxyl-protecting group; or a pharmacologically acceptable salt thereof. The compound (I) exhibits strong antibacterial activities, and especially, shows strong activities against MRSA. It is therefore useful not only as a general antibacterial agent but also as an antibacterial agent for MRSA against which no general antibacterial agents are recognized to be effective.