39546-32-2

Basic information

• Product Name: Hexahydroisonicotinamide
• Synonyms: Piperidine-4-carboxylic acid aMide;IsonipecotaMide, 98% 100GR;Isonipecotamide, 4-Carbamoylpiperidine, 4-(Aminocarbonyl)piperidine;4 - piperidine forMaMide;4-Piperidinecarboxamide 97%;Hexahydroisonicotimide;HEXAHYDROISONICOTINAMIDE;LABOTEST-BB LT00848032
• CAS NO: 39546-32-2
• Molecular Formula: C₆H₁₂N₂O
• Molecular Weight: 128.17
• EINECS: 254-501-6
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;C5 to C7;Chemical Synthesis;Heterocyclic Building Blocks;Piperidines;Heterocyclic Compounds;Piperazine;Pyrans, Piperidines & Piperazines;Amines
• Mol File: 39546-32-2.mol

Chemical Properties

• Melting Point: 145-148 °C(lit.)
• Boiling Point: 237.61°C (rough estimate)
• Flash Point: 142.3 °C
• Appearance: White to light yellow/Crystalline Powder
• Density: 1.0754 (rough estimate)
• Vapor Pressure: 0.000553mmHg at 25°C
• Refractive Index: 1.4880 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• PKA: 16.48±0.20(Predicted)
• Water Solubility: Soluble in water.
• Sensitive: Hygroscopic
• Stability: Hygroscopic
• BRN: 112554
• CAS DataBase Reference: Hexahydroisonicotinamide(CAS DataBase Reference)
• NIST Chemistry Reference: Hexahydroisonicotinamide(39546-32-2)
• EPA Substance Registry System: Hexahydroisonicotinamide(39546-32-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 39546-32-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Hexahydroisonicotinamide is used as a reactant for the synthesis of Survival motor neuron (SMN) protein modulators, which are crucial for the treatment of spinal muscular atrophy. It is also used in the synthesis of orally available naphthyridine protein kinase D inhibitors and heteroalicyclic carboxamidines as inhibitors of inducible nitric oxide synthase, both of which have potential therapeutic applications.
Used in Organic Synthesis:
Hexahydroisonicotinamide serves as a reactant for the preparation of phosphodiesterase 5 inhibitors, which are used in the treatment of various conditions, including erectile dysfunction and pulmonary arterial hypertension. Additionally, it is used as a reactant for the identification of small molecular inhibitors of importin-beta mediated nuclear import, which is an essential process in cellular function and regulation.
Used in Anesthetic and Analgesic Applications:
Hexahydroisonicotinamide is used as an anesthetic, analgesic, antimicrobial, and cooling agent for the prevention or treatment of skin irritation, providing relief and reducing discomfort in various medical and cosmetic applications.
Used in Antimicrobial Applications:
Hexahydroisonicotinamide's antimicrobial properties make it a valuable component in the development of products designed to combat microbial infections and maintain hygiene in various settings, including healthcare and personal care products.
Used in Cooling Agent Applications:
As a cooling agent, Hexahydroisonicotinamide is utilized in products that provide a cooling sensation, such as topical creams and lotions, offering temporary relief from discomfort and irritation caused by various skin conditions.

InChI:InChI=1/C6H12N2O/c7-6(9)5-1-3-8-4-2-5/h5,8H,1-4H2,(H2,7,9)/p+1

Upstream product

• 1453-82-3 isonicotinamide 
• 42596-58-7 piperidine-4-carboxylic acid hydrazide 
• 99706-49-7 piperidine-4-carboxylic acid-(N'-isopropyl-hydrazide) 
• 91419-48-6 4-carbamoyl-piperidine-1-carboxylic acid tert-butyl ester 
• 1126-09-6 4-carbethoxypiperidine 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 
• 142851-03-4 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate 
• 54-85-3 isoniazid 
• 64055-53-4 2-[2-(ethyloxy)phenyl]quinazoline-4(3H)-one 
• 2971-79-1 isonipecotic acid methyl ester 
• 498-94-2 isonipecotic acid 

Downstream Products

• 62718-28-9 1-methylpiperidine-4-carboxamide 
• 4395-98-6 4-cyanopiperidine 
• 93437-44-6 1-[3-(3-phenyl-[1,2,4]oxadiazol-5-yl)-propyl]-piperidine-4-carboxylic acid amide 
• 93997-44-5 1-{3-[3-(4-methoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-propyl}-piperidine-4-carboxylic acid amide 
• 62124-30-5 N-(2-hydroxyethyl)-4-carbamoylpiperidine 
• 72278-97-8 <2-<2-<4-(4-carbamoylpiperidino)butoxy>phenyl>ethyl>benzene 
• 129846-90-8 1,3-bis(4-aminocarbonyl-1-piperidinyl)propane 
• 129846-88-4 1-(3-chloropropyl)piperidine-4-carboxamide 
• 76447-96-6 1-(3-phenyl-2-propenyl)-4-piperidinecarboxamide 
• 86543-06-8 N-(3,4-dimethoxy-6-cyanophenyl)-N',N'-(3-carboxamidopentamethylene)thiourea 
• 178990-48-2 1-(2-phenyl-4-quinolinyl)-4-piperidinecarboxamide 
• 178990-30-2 1-[2-(2-Methoxy-phenyl)-quinolin-4-yl]-piperidine-4-carboxylic acid amide 
• 178990-31-3 1-[2-(2-Hydroxy-phenyl)-quinolin-4-yl]-piperidine-4-carboxylic acid amide 
• 103914-20-1 1-[6-fluoro-2-(4-fluorophenyl)-4-quinolinyl]-4-piperidinecarboxamide 

Relevant articles and documents

A General Catalyst Based on Cobalt Core–Shell Nanoparticles for the Hydrogenation of N-Heteroarenes Including Pyridines

Herein, we report the synthesis of specific silica-supported Co/Co3O4 core–shell based nanoparticles prepared by template synthesis of cobalt-pyromellitic acid on silica and subsequent pyrolysis. The optimal catalyst material allows for general and selective hydrogenation of pyridines, quinolines, and other heteroarenes including acridine, phenanthroline, naphthyridine, quinoxaline, imidazo[1,2-a]pyridine, and indole under comparably mild reaction conditions. In addition, recycling of these Co nanoparticles and their ability for dehydrogenation catalysis are showcased.

Hydrogenation of Pyridines Using a Nitrogen-Modified Titania-Supported Cobalt Catalyst

Novel heterogeneous catalysts were prepared by impregnation of titania with a solution of cobalt acetate/melamine and subsequent pyrolysis. The resulting materials show an unusual nitrogen-modified titanium structure through partial implementation of nitrogen into the support. The optimal catalyst displayed good activity and selectivity for challenging pyridine hydrogenation under acid free conditions in water as solvent.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a manufacturing method of nitrile. Compared with the prior art, the manufacturing method has the characteristics of significantly reduced using amount of an ammonia source, low environmental pressure, low energy consumption, low production cost, high purity and yield of a nitrile product and the like, and nitrile with a more complex structure can be obtained. The invention also relates to a method for manufacturing corresponding amine from nitrile.

INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL

The present invention provides compounds of Formula I and the pharmaceutically acceptable salts thereof, which are inhibitors of the ROMK (Kir1.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and chronic kidney disease and conditions associated with excessive salt and water retention.

The effect of substitution on the utility of piperidines and octahydroindoles for reversible hydrogen storage

Substituted piperidines and octahydroindoles are compared in terms of their usability as reversible organic hydrogen storage liquids for hydrogen-powered fuel cells. Theoretical Gaussian calculations indicate which structural features are likely to lower the enthalpy of dehydrogenation. Experimental results show that attaching electron donating or conjugated substituents to the piperidine ring greatly increases the rate of catalytic dehydrogenation, with the greatest rates being observed with 4-aminopiperidine and piperidine-4-carboxamide. Undesired side reactions were observed with some compounds such as alkyl transfer reactions during the dehydrogenation of 4-dimethylaminopiperidine, C-O and C-N cleavage reactions during hydrogenation and/or subsequent dehydrogenation of 4-alkoxy and 4-amino indoles, and disproportionation during the hydrogenation of 4-aminopyridine. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Method of treating a patient having precancerous lesions with phenyl quinazolinone derivatives

Derivatives of 2-phenyl quinazolinones are useful for the treatment of patients having precancerous lesions. These compounds are also useful to inhibit growth of neoplastic cells.

Novel potent antagonists of human neuropeptide Y Y5 receptors. Part 2: Substituted benzo[a]cycloheptene derivatives

Novel benzo[a]cycloheptene derivatives were prepared for the purpose of searching new neuropeptide Y-Y5 (NPY-Y5) receptor antagonists. The structure-activity relationships are described and compound 2o (FR226928) showed the most potent affinity for Y5 receptor of all we prepared and was found to have higher potency and better selectivity for Y5 over Y1 receptor affinities when compared with the known lead compound 1.

Improved functionalized resin for chemical synthesis

A support functionalized by an indole or pyrrole aldehyde is useful for the solid phase synthesis of amide type compounds.

QUINAZOLINONE ANTIANGINAL AGENTS

Compounds of formula: and pharmaceutically acceptable salts thereofwhereinR1 is H, Q - Q alkyl, C j -Q alkoxy or CONRsRs;R2 is H or- CJ-C4 alkyl;R3 is C2-C4 alkyl;R4 is H, C2-C4 alkanoyl optionally substituted withNR7R8, (hydroxy)C2-C4 alkyl optionally substitutedwith NR7R8, CH=CHC02R9, CH=CHCONR7R8,CH2CH2C02R9, CH2CH2CONR7R8, S02NR7R8,S02NH(CH2)nNR7R8 or imidazolyl;R5 and Rs are each independently H or C1-C4 alkyl;R7 and R8 are each independently H or C1-C4 alkyl, ortogether with the nitrogen atom to which they areattached form a pyrrolidino, piperidino, morpholino or4-(NR10)-l-piperazinyl group wherein any of saidgroups is optionally substituted with CONR5R6;R9 is H or C1-C4 alkyl;R10 is H, C1-C3 alkyl or (hydroxy)C2-C3 alkyl; andn is 2, 3 or 4;with the proviso that R4 is not H when R1 is H, C1-C4 alkylor C1-C4 alkoxy; are selective cGMP PDE inhibitors usefiilin the treatment of cardiovascular disorders such as angina, hypertension, heart failure and atherosclerosis.

Facile Reduction of Pyridines with Nickel-Aluminum Alloy

Nickel-aluminum alloy in dilute base can be used to reduce a variety of pyridines, quinolines, and isoquinoline to the corresponding piperidines, 1,2,3,4-tetrahydroquinolines, and 1,2,3,4-tetrahydroisoquinoline in good yield.The reaction is simple to perform, and high temperatures, high pressures, or hydrogen atmospheres are not required.The reaction is accelerated by substituents in the 2-position and by electron-withdrawing groups in the 3- and 4-positions while electron-supplying groups in the 3- and 4-positions retard the reaction.The major product isolated from the reduction of 2-phenylpyridine was 2-cyclohexylpiperidine hydrochloride.With isoniazid (1) and iproniazid (4) the pyridine ring is hydrogenated before the hydrazine is cleaved.