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
• Article Data: 8

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

Chemical Properties

YELLOW CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 4138-26-5 differently. You can refer to the following data:
1. Reactant for synthesis of:? ;DPP-4 inhibitors1? ;IKKβ inhibitors2? ;Spiroimidazolidinone NPC1L1 inhibitors3? ;Sulfamides4? ;Phosphodiesterase 5 inhibtors5? ;Anti-HIV agents6
2. Nipecotamide, is a budiling blcok used in the sythnesis of various compounds, such as DPP-4 inhibitors, IKKβ inhibitors, piroimidazolidinone NPC1L1 inhibitors, and Anti-HIV agents.

Definition

ChEBI: The amide resulting from the formal condensation of nipecotic acid with ammonia.

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

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

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 
• 1050446-96-2 (R)-1-(p-methylbenzoyl)nipecotamide 
• 915226-43-6 (R)-tert-butyl 3-carbamoylpiperidine-1-carboxylate 
• 1050446-95-1 (R)-1-benzoylnipecotamide 
• 168749-30-2 (R)-piperidine-3-carboxamide 
• 498-95-3 (R)-nipecotic acid 
• 498-95-3 (S)-nipecotic acid 
• 88495-55-0 (S)-piperidine-3-carboxamide 
• 1050446-97-3 (R)-1-(p-chlorobenzoyl)nipecotamide 
• 1192711-39-9 1-(2-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-3-carboxamide 
• 957438-22-1 C₂₄H₃₂N₆O₂ 
• 940871-27-2 1-(6-(2-(3-(5-t-butyl-2-p-tolyl-2H-pyrazol-3-yl)-ureidomethyl)phenoxy)pyrimidin-4-yl)piperidin-3-carboxylic amide 

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.

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.

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.