132363-97-4

Upstream product

• 13141-42-9 2-(2-phenylethynyl)pyridine 
• 6280-87-1 δ-chlorovaleronitrile 
• 103-63-9 1-phenyl-2-bromoethane 
• 110-89-4 piperidine 
• 100-42-5 styrene 
• 132363-97-4 2-(2-phenylethyl)piperidine 
• 214267-24-0 1-((S)-3-Phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-yl)-1H-benzotriazole 
• 111-30-8 Glutaraldehyde 
• 214267-46-6 (3S,5S)-5-Phenethyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine 
• 132363-96-3 1-Phenyl-2-[(S)-1-((S)-1-phenyl-ethyl)-piperidin-2-yl]-ethanol 
• 100-52-7 benzaldehyde 
• 109-06-8 α-picoline 
• 538-49-8 2-[(E)-2-phenylethenyl]pyridine 
• 538-49-8 2-styrylpyridine 

Downstream Products

• 132363-97-4 (2S)-(-)-2-(2-phenylethyl)piperidine 
• 101113-68-2 (+/-)-sedaminone 
• 1145683-18-6 (R)-4-methyl-2-[5-(2-phenethyl-piperidin-1-yl)-4'-trifluoromethyl-biphenyl-3-yl]-pentanoic acid methyl ester 
• 857940-38-6 2-Phenethyl-1-((E)-3-phenyl-allyl)-piperidine 
• 1346681-87-5 (2R)-1-(3-mesitylpropanoyl)-2-(2-phenylethyl)piperidine 

Relevant academic research and scientific papers

Titanium(III)-induced transformation of hydroxylamines to imines or secondary amines

N,N-Disubstituted and cyclic hydroxylamines can be converted into the corresponding imines efficiently upon treatment with anhydrons titanium trichloride in THF at room temperature. Similar treatment of N-allylhydroxylamines with anhydrous titanium trichloride gives 1-azadienes, which are versatile synthetie intermediates for aza-Diels-Alder reactions. On the other hand, the same hydroxylamines can be converted into the corresponding secondary amines upon treatment with aqueous titanium trichloride in methanol. It is noteworthy that optically active hydroxylamines, which have chirality at the α-position to nitrogen, can be converted into optically active secondary amines without loss of chirality. Dihydro-2(1H)-quinolinones can be prepared upon treatment of 1-hydroxy-3,4-dihydro-2(1H)-quinolinones with aqueous titanium trichloride. The substrates of N,N-disubstituted and cyclic hydroxylamines can be prepared readily upon treatment of nitrones with nucleophiles. Since nitrones can be prepared by metal-catalyzed oxidations of secondary amines with hydrogen peroxide, the present titanium(III)-promoted reaction of hydroxylamines will provide a convenient method for the synthesis of either α-substituted imines or amines from secondary amines.

Direct, Catalytic α-Alkylation of N-Heterocycles by Hydroaminoalkylation: Substrate Effects for Regiodivergent Product Formation

Saturated N-heterocycles are prevalent in pharmaceutical and agrochemical industries, yet remain challenging to catalytically alkylate. Most strategies for C-H activation of these challenging substrates use protected amines or high loadings of precious me

GROUP 5 METAL COMPLEXES FOR PRODUCING AMINE-FUNTIONALIZED POLYOLEFINS

This application pertains to group 5 metal complexes having the structure of Formula I: and their potential utility in catalyzing amination of polyolefins having alkene groups.amine-

GROUP 5 METAL COMPLEXES FOR CATALYTIC AMINE FUNCTIONALIZATION

This application pertains to group 5 metal complexes having the structure of Formula I; and their potential utility in catalyzing α-alkylation of secondary amine-containing moieties.

Combined Imine Reductase and Amine Oxidase Catalyzed Deracemization of Nitrogen Heterocycles

A novel amine oxidase (AO)/imine reductase (IRED) system was developed for the deracemization of racemic amines. By combining (R)-6-hydroxy-d-nicotine oxidase (6-HDNO) with an (R)-IRED, a panel of racemic 2-substituted piperidines and pyrrolidines were deracemized to yield the (S)-amines in high yields and enantiomeric excess values. Other N-heterocycles were deracemized with monoamine oxidase (MAO-N) or 6-HDNO in combination with ammonia borane, which allowed comparison of the two enzyme deracemization approaches with that involving a chemical reducing agent.

Development of an R-selective amine oxidase with broad substrate specificity and high enantioselectivity

Amine oxidases are useful bio-catalysts for the synthesis of enantiomerically pure 1°, 2° and 3° chiral amines. Enzymes in this class (e.g., MAO-N from Aspergillus niger) reported previously have been shown to be highly S selective. Herein we report the development of an enantiocomplementary R-selective amine oxidase based on 6-hydroxy-D-nicotine oxidase (6-HDNO) with broadened substrate scope and high enantioselectivity. The engineered 6-HDNO enzyme has been applied to the preparative deracemisation of a range of racemic amines to yield S-configured products, for example, (S)-nicotine, in high ee. Nicotine rush: An R-selective amine oxidase based on 6-hydroxy-D-nicotine oxidase (6-HDNO) with broadened substrate scope and high enantioselectivity has been developed. The engineered 6-HDNO enzyme is applied to the preparative deracemization of a range of racemic amines to yield S-configured products, for example, (S)-nicotine, in high ee.

Lobelane analogues as novel ligands for the vesicular monoamine transporter-2

A series of lobelane analogues has been synthesized and their structure-activity relationships at the vesicular monoamine transporter-2 (VMAT2) have been evaluated. The most potent analogues in this series were the cis-2,6-piperidino analogues, 25b, 27b, 28b, and 30b, with Ki values ranging from 430 to 580 nM.

2-substituted piperidines that are ligands for monoamine receptors and transporters

One aspect of the present invention relates to heterocyclic compounds. A second aspect of the present invention relates to the use of the heterocyclic compounds as ligands for various mammalian cellular receptors, including dopamine, serotonin, or norepinephrine transporters. The compounds of the present invention will find use in the treatment of numerous ailments, conditions and diseases which afflict mammals, including but not limited to addiction, anxiety, depression, sexual dysfunction, hypertension, migraine, Alzheimer's disease, obesity, emesis, psychosis, analgesia, schizophrenia, Parkinson's disease, restless leg syndrome, sleeping disorders, attention deficit hyperactivity disorder, irritable bowel syndrome, premature ejaculation, menstrual dysphoria syndrome, urinary incontinence, inflammatory pain, neuropathic pain, Lesche-Nyhane disease, Wilson's disease, and Tourette's syndrome. An additional aspect of the present invention relates to the synthesis of combinatorial libraries of the heterocyclic compounds, and the screening of those libraries for biological activity, e.g., in assays based on dopamine transporters.

Efficient Routes to Chiral 2-Substituted and 2,6-Disubstituted Piperidines

The syntheses of chiral 2-substituted and 2,6-disubstituted piperidines, and piperidin-2-ylphosphonates, via benzotriazole methodology are described.

Radical cyclisations of imines and hydrazones

Radical cyclisation of sp3 carbon-centred radicals onto imines and hydrazones provides a new method for the synthesis of 5- and 6-membered ring nitrogen heterocycles. Cyclisation onto the electrophilic carbon of the C=N group and 5-exo stereoelectronic selectivity are the dominating mechanistic parameters. The C-centred radical intermediates were generated from benzeneselenyl precursors using Bu3SnH.