3319-01-5

Basic information

• Product Name: 1-CYCLOHEXYLPIPERIDINE
• Synonyms: 1-CYCLOHEXYLPIPERIDINE;CYCLOHEXYL PIPERIDINE;1-cyclohexyl-piperidin;1-Piperidinocyclohexane;N-Cyclohexylpiperidine
• CAS NO: 3319-01-5
• Molecular Formula: C₁₁H₂₁N
• Molecular Weight: 167.29
• EINECS: 222-016-9
• Mol File: 3319-01-5.mol

Chemical Properties

• Melting Point: 73-74 °C(Solv: benzene (71-43-2); ligroine (8032-32-4)(1:5))
• Boiling Point: 231-234°C
• Flash Point: 231-234°C
• Appearance: /
• Density: 0,914 g/cm3
• Vapor Pressure: 0.0531mmHg at 25°C
• Refractive Index: 1.4856
• PKA: 10.07±0.20(Predicted)
• Water Solubility: Immiscible with water.
• BRN: 105594
• CAS DataBase Reference: 1-CYCLOHEXYLPIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CYCLOHEXYLPIPERIDINE(3319-01-5)
• EPA Substance Registry System: 1-CYCLOHEXYLPIPERIDINE(3319-01-5)

Safety Data

• Statements: 36/38
• Safety Statements: 26-36
• RTECS: TM6520000
• Hazardous Substances Data: 3319-01-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Cyclohexylpiperidine is used as a key intermediate in the synthesis of 1-(1-phenylcyclohexyl)piperidine, which exhibits anticholinesterase activity and antagonistic activity to acetylcholine. This makes it a valuable compound in the development of medications targeting neurological disorders.
Used in Neurological Applications:
1-Cyclohexylpiperidine is used as a N-methyl-D-aspartate receptor (NMDAR) antagonist, which plays a crucial role in modulating the excitatory neurotransmission in the central nervous system. Its antagonistic properties make it a potential candidate for the treatment of conditions such as Alzheimer's disease, Parkinson's disease, and other neurodegenerative disorders.
Used in Veterinary Medicine:
1-Cyclohexylpiperidine is used as an anesthetic for animals, providing a safe and effective means of sedation and pain relief during medical procedures and surgeries. Its anesthetic properties make it a valuable asset in the veterinary field, ensuring the well-being and comfort of animals undergoing treatment.

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 1597, 1950 DOI: 10.1021/ja01160a046Tetrahedron, 52, p. 10835, 1996 DOI: 10.1016/0040-4020(96)00631-X

InChI:InChI=1/C11H21N/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h11H,1-10H2

Upstream product

• 110-89-4 piperidine 
• 108-85-0 1-bromocyclohexane 
• 107-31-3 Methyl formate 
• 108-94-1 cyclohexanone 
• 108-93-0 cyclohexanol 
• 2981-10-4 1-(cyclohex-1-en-1-yl)piperidine 
• 61862-37-1 (2-cyclohexen-1-yl)piperidine 
• 857483-65-9 5-cyclohexylamino-valeronitrile 
• 111-24-0 1,5-dibromo-pentane 
• 108-91-8 cyclohexylamine 
• 56528-77-9 (+/-)-2-cyclohexyl-piperidine 
• 110-82-7 cyclohexane 
• 3867-15-0 1-piperidinocyclohexylcarbonitrile 
• 111-29-5 1 ,5-pentanediol 

Downstream Products

• 41225-71-2 1-cyclohexyl-1-methyl-piperidinium; iodide 
• 599-05-3 perfluoro-(1-hexylpiperidine) 
• 60234-15-3 perfluoro-N-cyclohexylpiperidine 

Relevant articles and documents

Aggregation Behavior of a Six-Membered Cyclic Frustrated Phosphane/Borane Lewis Pair: Formation of a Supramolecular Cyclooctameric Macrocyclic Ring System

A new six-membered cyclic frustrated phosphane/borane Lewis pair was liberated from its HB(C6F5)2 adduct by treatment with vinylcyclohexane. The system is an active frustrated Lewis pair that undergoes cycloaddition reactions with suitable π reagents and it splits dihydrogen. At room temperature in solution the new compound is a monomer, however, in the crystal and in solution at low temperature it aggregates to a thermodynamically favoured supramolecular macrocyclic cyclooctamer.

Iridium and bis(4-nitrophenyl)phosphoric acid catalysed amination of diol by hydrogen-borrowing methodology for the synthesis of cyclic amine: Synthesis of clopidogrel

The borrowing hydrogen method is an environmentally benign process for the synthesis of amines, as H2O is the side product. A new green process for the amination of diol by [Ir] catalyst 15 and bis(4-nitrophenyl)phosphoric acid for the synthesis of cyclic amine is reported. This method was successfully applied for the synthesis of antiplatelet drug clopidogrel.

Bidentate NHC-Cobalt Catalysts for the Hydrogenation of Hindered Alkenes

Herein, we report a series of easily accessible bidentate N-heterocyclic carbene (NHC) cobalt catalysts, which enable the hydrogenation of hindered alkenes under mild conditions. The four-coordinated bidentate NHC-Co(II) complexes were characterized by X-ray diffraction, elemental analysis, ESI-HRMS, and magnetic moment measurements, revealing a distorted-tetrahedral geometry and a high-spin configuration of the metal center. The activity of the in situ formed catalytic system, which was obtained from easily available NHC precursors, CoCl2, and NaHBEt3, was identical with those of well-defined NHC-cobalt catalysts. This highlights the potential utility of this reaction system.

Ni-Catalyzed reductive amination of phenols with ammonia or amines into cyclohexylamines

Phenol and its derivatives, which naturally occur in lignocellulose, can be considered as a renewable feedstock not only for aromatic, but also for alicyclic compounds, such as primary and N-substituted cyclohexylamines. So far, the latter are mostly produced from non-renewable starting materials like benzene via problematic nitration/reduction or cross-coupling routes. Herein, an efficient reductive amination of phenol with ammonia or amines is demonstrated, for the first time without the need for rare and expensive noble metals and without using any additives. Various supported Ni catalysts were screened and we elucidated the influence of the key parameters, including the acid-base properties of the supporting material. Acquired knowledge was then applied to different phenol-ammonia/amine combinations, resulting in the synthesis of various primary, secondary and tertiary cyclohexylamines in fair to very high yields.

Colloidal and Nanosized Catalysts in Organic Synthesis: XXIII. Reductive Amination of Carbonyl Compounds Catalyzed by Nickel Nanoparticles in a Plug-Flow Reactor

Reductive amination of aldehydes and ketones with primary and secondary amines under catalysis with nickel nanoparticles supported on zeolite X, MgO, or activated carbon in the gas phase or in the gas-liquid system in a plug-flow reactor proceeds at atmospheric pressure of hydrogen with the formation of secondary or tertiary amines in high yield.

Synthesis method for converting lignin 4-O-5 model compound diaryl ether into nitrogen-containing compound

The invention discloses a synthesis method for converting lignin 4-O-5 model compound diaryl ether into a nitrogen-containing compound. According to the synthesis method, a diaryl ether compound andan amine compound are subjected to a heating reaction in a certain amount of a solvent (containing a certain amount of water) in an argon atmosphere (containing a certain amount of air) under the actions of a metal catalyst and sodium borohydride, such that the drug with the important physiological activity or the compound with the natural product skeleton containing nitrogen is formed by directlycoupling the C-O bond cut and the amine compound cross while the corresponding aromatic hydrocarbon is obtained. According to the present invention, the synthesis method has characteristics of simpleand easily-available raw materials, high conversion rate, important product and good yield, and has broad application prospects in the degradation and deep development and utilization of lignin.

Palladium-Catalyzed Formal Cross-Coupling of Diaryl Ethers with Amines: Slicing the 4-O-5 Linkage in Lignin Models

Lignin is the second most abundant organic matter on Earth, and is an underutilized renewable source for valuable aromatic chemicals. For future sustainable production of aromatic compounds, it is highly desirable to convert lignin into value-added platform chemicals instead of using fossil-based resources. Lignins are aromatic polymers linked by three types of ether bonds (α-O-4, β-O-4, and 4-O-5 linkages) and other C?C bonds. Among the ether bonds, the bond dissociation energy of the 4-O-5 linkage is the highest and the most challenging to cleave. To date, 4-O-5 ether linkage model compounds have been cleaved to obtain phenol, cyclohexane, cyclohexanone, and cyclohexanol. The first example of direct formal cross-coupling of diaryl ether 4-O-5 linkage models with amines is reported, in which dual C(Ar)?O bond cleavages form valuable nitrogen-containing derivatives.

REACTIONS OF STANNYL CATIONS

The present invention relates to a method of reducing, cleaving and/or coupling at least one C=O, C-O, C=C or C=N bond of a compound, using a reagent comprising a stannyl cation.

Colloid and Nanosized Catalysts in Organic Synthesis: XVIII.1 Disproportionation and Cross-Coupling of Amines During Catalysis with Immobilized Nickel Nanoparticles

It has been stated that immobilized nickel nanoparticles catalyze disproportionation and cross-coupling of amines. The influence of the support on the catalysis of these properties in the in plug-flow reactor has been studied. The use of active carbon as the support has been found advantageous for the cross-coupling of amines, whereas alumina was a better support for the disproportionation reaction.

Catalytic intermolecular hydroaminations of unactivated olefins with secondary alkyl amines

The intermolecular hydroamination of unactivated alkenes with simple dialkyl amines remains an unsolved problem in organic synthesis. We report a catalytic protocol for efficient additions of cyclic and acyclic secondary alkyl amines to a wide range of alkyl olefins with complete anti-Markovnikov regioselectivity. In this process, carbon-nitrogen bond formation proceeds through a key aminium radical cation intermediate that is generated via electron transfer between an excited-state iridium photocatalyst and an amine substrate. These reactions are redox-neutral and completely atom-economical, exhibit broad functional group tolerance, and occur readily at room temperature under visible light irradiation. Certain tertiary amine products generated through this method are formally endergonic relative to their constituent olefin and amine starting materials and thus are not accessible via direct coupling with conventional ground-state catalysts.