35193-73-8

Usage

Uses

Used in Pharmaceutical Industry:
(-)-2-(2,2-dicyclohexylethyl)piperidine is used as a chiral ligand in asymmetric synthesis for the development of new pharmaceutical drugs. Its stereochemistry plays a crucial role in the selectivity and efficacy of synthesized compounds, contributing to the creation of more effective medications.
Used in Organic Synthesis:
In the realm of organic synthesis, (-)-2-(2,2-dicyclohexylethyl)piperidine serves as a valuable building block. Its unique structure allows for the construction of complex organic molecules, facilitating advancements in chemical research and the development of novel compounds.
Used in Anti-inflammatory and Analgesic Applications:
Due to its anti-inflammatory and analgesic effects, (-)-2-(2,2-dicyclohexylethyl)piperidine is a potential candidate for the development of new pharmaceutical drugs targeting pain and inflammation. Its properties could lead to the creation of more effective treatments for various conditions that involve these symptoms.

Upstream product

• 5733-76-6 α-(2,2-diphenylvinyl)pyridine 
• 5749-71-3 2-(2,2-dicyclohexylvinyl)pyridine 
• 18368-63-3 6-chloro-2-picoline 
• 119-60-8 dicyclohexyl ketone 
• 110-87-2 3,4-dihydro-2H-pyran 
• 3626-67-3 C₁₉H₃₃N 
• 4221-03-8 5-hydroxypentanal 
• 1029019-96-2 tert-butyl N-(5-oxopentyl)-N-[(R)-(1-phenylethyl)]carbamate 
• 773070-58-9 ethyl {(2S)-1-[(1R)-1-phenylethyl]piperidin-2-yl}acetate 
• 931-51-1 cyclohexylmagnesiumchloride 
• 3626-67-3 (R)-2-(2,2-dicyclohexylvinyl)piperidine 
• 254427-95-7 ethyl {(2R)-1-[(1S)-1-phenylethyl]piperidin-2-yl}acetate 

Relevant academic research and scientific papers

Asymmetric Synthesis and Absolute Configuration of (+)- and (-)-Perhexiline

Racemic perhexiline has been used (or is currently undergoing clinical trials) for the treatment of a variety of cardiovascular disorders. Increasing evidence suggests that the (-)-enantiomer should be used, as opposed to the racemic mixture. Here, we report the first asymmetric synthesis of both enantiomers of perhexiline in high enantiomeric excess and the assignment of their (-)-S/(+)-R absolute stereochemistry by X-ray crystallography.

(+)-(R)- and (?)-(S)-Perhexiline maleate: Enantioselective synthesis and functional studies on Schistosoma mansoni larval and adult stages

Schistosomiasis is a neglected tropical disease mainly affecting the poorest tropical and subtropical areas of the world with the impressive number of roughly 200 million infections per year. Schistosomes are blood trematode flukes of the genus Schistosoma causing symptoms in humans and animals. Organ morbidity is caused by the accumulation of parasite eggs and subsequent development of fibrosis. If left untreated, schistosomiasis can result in substantial morbidity and even mortality. Praziquantel (PZQ) is the most effective and widely used compound for the treatment of the disease, in prevention and control programs in the last 30 years. Unfortunately, it has no effect on juvenile immature schistosomes and cannot prevent reinfection or interfere with the schistosome life cycle; moreover drug-resistance represents a serious threat. The search for an alternative or complementary treatment is urgent and drug repurposing could accelerate a solution. The anti-anginal drug perhexiline maleate (PHX) has been previously shown to be effective on larval, juvenile, and adult stages of S. mansoni and to impact egg production in vitro. Since PHX is a racemic mixture of R-(+)- and S-(?)-enantiomers, we designed and realized a stereoselective synthesis of both PHX enantiomers and developed an analytical procedure for the direct quantification of the enantiomeric excess also suitable for semipreparative separation of PHX enantiomers. We next investigated the impact of each enantiomer on viability of newly transformed schistosomula (NTS) and worm pairs of S. mansoni as well as on egg production and vitellarium morphology by in vitro studies. Our results indicate that the R-(+)-PHX is mainly driving the anti-schistosomal activity but that also the S-(?)-PHX possesses a significant activity towards S. mansoni in vitro.

Influence of [2H]-labelled acetic acid as solvent in the synthesis of [2H]-labelled perhexiline

Preparation of deuterium-labelled perhexiline from an unsaturated analogue was performed via reduction with deuterium gas and PtO2 in acetic acid. Low incorporation was observed when using acetic acid as solvent (most abundant mass peak was MD0+ ), but when changing the solvent to deuterium-labelled acetic acid, e.g. acetic acid-OD or acetic acid-d4, a higher incorporation was observed (most abundant mass peak was MD8+). Using hydrogen gas instead of deuterium gas withdeuterium-labelled acetic acid, high levels of deuterium incorporation were observed (most abundant mass peak was MD5+). An attempt to reduce a precursor with a fully deuterated pyridine to obtain perhexiline with a higher content of deuterium failed. Copyright

Process for preparing 2-(2,2-dicyclohexylethyl)piperidine

2-(2,2-Dicyclohexylethyl)piperidine is prepared via the catalytic hydrogenation of 2-(2,2-diphenylethenyl)pyridine in a single step. High yields are obtained using an anhydrous Raney nickel catalyst.