Nipecotamide

Base Information

• Chemical Name: Nipecotamide
• CAS No.: 4138-26-5
• Molecular Formula: C6H12N2O
• Molecular Weight: 128.174
• Hs Code.: 29339900
• European Community (EC) Number: 223-962-5
• NSC Number: 523303
• DSSTox Substance ID: DTXSID601313721
• Nikkaji Number: J208.768E
• Wikidata: Q27127086
• ChEMBL ID: CHEMBL1546193
• Mol file: 4138-26-5.mol

Synonyms:nipecotic acid amide;nipecotic acid amide maleate (1:1), (+-)-isomer;nipecotic acid amide, (+-)-isomer

Chemical Property of Nipecotamide

Chemical Property:

• Appearance/Colour: yellow crystalline powder
• Vapor Pressure: 0.000553mmHg at 25°C
• Melting Point: 103-106 °C(lit.)
• Refractive Index: 1.4880 (estimate)
• Boiling Point: 311.7 °C at 760 mmHg
• PKA: 16.50±0.20(Predicted)
• Flash Point: 142.3 °C
• PSA: 55.12000
• Density: 1.06 g/cm³
• LogP: 0.50040
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 128.094963011
• Heavy Atom Count: 9
• Complexity: 114

Purity/Quality:

99% ^*data from raw suppliers

Nipecotamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CNC1)C(=O)N
• Uses: Reactant for synthesis of:? ;DPP-4 inhibitors1? ;IKKβ inhibitors2? ;Spiroimidazolidinone NPC1L1 inhibitors3? ;Sulfamides4? ;Phosphodiesterase 5 inhibtors5? ;Anti-HIV agents6 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.

Technology Process of Nipecotamide

There total 5 articles about Nipecotamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.4%

nicotinamide (98-92-0,1255150-40-3) → nipecotamide (4138-26-5,168749-30-2)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In isopropyl alcohol; at 75 ℃; for 4h; under 3750.38 Torr;

Reference yield: 70.0%

nicotinamide (98-92-0,1255150-40-3) → nipecotamide (4138-26-5,168749-30-2) + 1,4,5,6-tetrahydropyridine-3-carboxamide (7032-11-3)

Guidance literature:

With palladium on carbon type-K; hydrogen; In methanol; at 40 ℃; for 21h; under 750.075 Torr; Temperature; Pressure; Autoclave;

DOI:10.1021/acs.oprd.0c00544

Reference yield:

1,4,5,6-tetrahydropyridine-3-carboxamide (7032-11-3) → nipecotamide (4138-26-5,168749-30-2)

Guidance literature:

With chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen; In methanol; at 50 ℃; for 20h; under 7500.75 Torr; Reagent/catalyst;

DOI:10.1021/acs.oprd.0c00544

upstream raw materials:

nicotinamide hydrochloride

nicotinamide

1,4,5,6-tetrahydropyridine-3-carboxamide

Downstream raw materials:

1'-benzyl-[1,4']bipiperidinyl-3-carboxylic acid amide

4-(3-carbamoyl-piperidin-1-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester

tert-butyl 3-carbamoylpiperidine-1-carboxylate

3-Aminomethylpiperidine

Refernces

• 1、 Beller, Matthias,Chandrashekhar, Vishwas G.,Jagadeesh, Rajenahally V.,Kreyenschulte, Carsten,Murugesan, Kathiravan. "A General Catalyst Based on Cobalt Core–Shell Nanoparticles for the Hydrogenation of N-Heteroarenes Including Pyridines". supporting information. p. 17408 - 17412. Retrieved 2020/08/21.
• 2、 Maegawa, Tomohiro,Akashi, Akira,Yaguchi, Kiichiro,Iwasaki, Yohei,Shigetsura, Masahiro,Monguchi, Yasunari,Sajiki, Hironao. "Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions". experimental part. p. 6953 - 6963. Retrieved 2010/02/28.