4138-26-5

Basic information

• Product Name: NIPECOTAMIDE
• Synonyms: HEXAHYDRONICOTINAMIDE;3-PIPERIDINECARBOXAMIDE;NIPECOTAMIDE;PIPERIDINE-3-CARBOXAMIDE;TIMTEC-BB SBB004239;Nipecotamide,97%;nipecotic acid amide;3-Piperdine carboxamide
• CAS NO: 4138-26-5
• Molecular Formula: C₆H₁₂N₂O
• Molecular Weight: 128.17
• EINECS: 223-962-5
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Building Blocks;Heterocyclic Building Blocks;Piperidines;C5 to C7;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 4138-26-5.mol

Chemical Properties

• Melting Point: 103-106 °C(lit.)
• Boiling Point: 237.61°C (rough estimate)
• Flash Point: 142.3 °C
• Appearance: 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
• PKA: 16.50±0.20(Predicted)
• CAS DataBase Reference: NIPECOTAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: NIPECOTAMIDE(4138-26-5)
• EPA Substance Registry System: NIPECOTAMIDE(4138-26-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 4138-26-5(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
NIPECOTAMIDE is used as a reactant for the synthesis of various compounds for different therapeutic applications.
2. Used in DPP-4 Inhibitors Synthesis:
NIPECOTAMIDE is used as a building block for the synthesis of DPP-4 inhibitors, which are important in the treatment of type 2 diabetes.
3. Used in IKKβ Inhibitors Synthesis:
NIPECOTAMIDE is used as a building block for the synthesis of IKKβ inhibitors, which have potential applications in the treatment of inflammatory diseases and cancer.
4. Used in Spiroimidazolidinone NPC1L1 Inhibitors Synthesis:
NIPECOTAMIDE is used as a building block for the synthesis of spiroimidazolidinone NPC1L1 inhibitors, which are being investigated for their potential role in cholesterol absorption and related conditions.
5. Used in Sulfamates Synthesis:
NIPECOTAMIDE is used as a building block for the synthesis of sulfamates, which are a class of compounds with various applications in the pharmaceutical industry.
6. Used in Phosphodiesterase 5 Inhibitors Synthesis:
NIPECOTAMIDE is used as a building block for the synthesis of phosphodiesterase 5 inhibitors, which are commonly used in the treatment of erectile dysfunction and pulmonary arterial hypertension.
7. Used in Anti-HIV Agents Synthesis:
NIPECOTAMIDE is used as a building block for the synthesis of anti-HIV agents, which are crucial in the fight against the human immunodeficiency virus (HIV).

InChI:InChI=1/C6H12N2O/c7-6(9)5-2-1-3-8-4-5/h5,8H,1-4H2,(H2,7,9)/p+1/t5-/m0/s1

Upstream product

• 25334-23-0 nicotinamide hydrochloride 
• 98-92-0 nicotinamide 
• 7032-11-3 1,4,5,6-tetrahydropyridine-3-carboxamide 

Downstream Products

• 110454-64-3 (2R,9R)-4,4-Diphenyl-1,7-diaza-tricyclo[7.3.1.0^2,7]tridec-5-en-8-one 
• 110392-28-4 (2R,9S)-4,4-Diphenyl-1,7-diaza-tricyclo[7.3.1.0^2,7]tridec-5-en-8-one 
• 89122-53-2 1-{4-[2-((E)-Styryl)-phenoxy]-butyl}-piperidine-3-carboxylic acid amide 
• 197654-12-9 1-[2-(4-Chloro-benzoyl)-4-nitro-phenyl]-piperidine-3-carboxylic acid amide 
• 259268-47-8 N-(4-fluorophenylethyl)-3-piperidinecarboxamide 
• 259268-48-9 N-(3-phenylpropyl)-3-piperidinecarboxamide 
• 259268-42-3 N-[2-(bisphenylmethoxy)ethyl]-3-piperidinecarboxamide 
• 184969-01-5 1'-benzyl-[1,4']bipiperidinyl-3-carboxylic acid amide 
• 340962-96-1 4-(3-carbamoyl-piperidin-1-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 91419-49-7 tert-butyl 3-carbamoylpiperidine-1-carboxylate 
• 226249-39-4 3-carbamoyl-1-(4-chlorobenzyl)piperidine 
• 947304-21-4 C₃₂H₄₄N₄O₅ 
• 162167-97-7 tert-butyl 3-(aminomethyl)piperidine-1-carboxylate 
• 274682-80-3 3-thiocarbamoylpiperidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Development and Scale-Up of an Asymmetric Synthesis Process for Alogliptin

Alogliptin (1) benzoate is a potent, highly selective inhibitor of serine protease dipeptidyl-peptidase IV, approved by US FDA for the treatment of type 2 diabetes. Herein, we report a more cost-effective process that includes ruthenium-catalyzed asymmetric hydrogenation followed by Hofmann rearrangement of 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile (10) to introduce a chiral amino moiety at a late stage. Use of an inexpensive and readily available nicotinamide (6) for a chiral aminopiperidine core and iodobenzene diacetate (PIDA) under mild and specific conditions allowed us to access 1 with excellent total yield and comparable quality to that manufactured by the original process.

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.

PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE NIPECOTAMIDE

Optically active nipecotamide can be produced by a method for producing optically active nipecotamide comprising: a step of reacting nipecotamide with optically active lactic acid to prepare a mixture of diastereomer salts and then allowing one diastereomer salt in the mixture of the diastereomer salts to precipitate; a step of collecting the precipitated diastereomer salt; and, a step of treating the collected diastereomer salt with a base to cause optically active nipecotamide to release.

Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions

An efficient and practical arene hydrogenation procedure based on the use of heterogeneous platinum group catalysts has been developed. Rh/C is the most effective catalyst for the hydrogenation of the aromatic ring, which can be conducted in iPrOH under neutral conditions and at ordinary to medium H 2 pressures (10 atm). A variety of arenes such as alkylbenzenes, benzoic acids, pyridines, furans, are hydrogenated to the corresponding cyclohexyl and heterocyclic compounds in good to excellet yields. The use of Ru/C, less expensive than Rh/C, affords an effective and practical method for the hydrogenation of arenes including phenols. Both catalysts can be reused several times after simple filtration without any significant loss of catalytic activity.

Microwave-assisted hydrogenation of pyridines

Using a commercially available device for controlled introduction of hydrogen in a vial for reactions under microwave dielectric heating, we developed a protocol for the transformation of substituted pyridines into the corresponding piperidines. Complete reduction occurred in 40 minutes, or even less, on substrates that require 24-48 hours to be reduced under standard conditions. Moreover, the reduction proved to be as stereoselective as the corresponding reaction carried out at room temperature. Georg Thieme Verlag Stuttgart.

A mild and facile method for complete hydrogenation of aromatic nuclei in water

A mild and complete hydrogenation of aromatic rings catalyzed by heterogeneous 10% Rh/C proceeds at 80 °C in water under 5 atm of H 2 pressure. This method is applicable to the hydrogenation of various carbon and heteroaromatic compounds such as alkylbenzenes, biphenyls, pyridines and furans. Georg Thieme Verlag Stuttgart.

METHOD FOR TREATING CHRONIC PAIN USING MEK INHIBITORS

The invention features a method for treating chronic pain using a compound selected from formulae (I), (II)A, (I)B and (I)C.

Benzenesulfonamide derivatives and their use as MEK inhibitors

Benzenesulfonamides of formula (I), in which W is OR1, NR2OR1, NRARB, NR2NRARB, or NR2(CH2)2-4NRARBand the other variables as defined in the claims, are inhibitors of MEK and are effective in the treatment of proliferative diseases, cancer, stroke, heart failure, xenograft rejection, arthritis, cystic fibrosis, hepatomegaly, cardiomegaly, Alzheimer's disease, complications of diabetes, septic shock, and viral infection.