NIPECOTAMIDE Chemical Properties

Melting point:

103-106 °C(lit.)

Boiling point:

237.61°C (rough estimate)

Density 

1.0754 (rough estimate)

refractive index 

1.4880 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

16.50±0.20(Predicted)

form 

Crystalline Powder

color 

Yellow

InChI

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

InChIKey

BVOCPVIXARZNQN-UHFFFAOYSA-N

SMILES

N1CCCC(C(N)=O)C1

CAS DataBase Reference

4138-26-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

NIPECOTAMIDE Usage And Synthesis

Chemical Properties

YELLOW CRYSTALLINE POWDER

Uses

Reactant for synthesis of:• ;DPP-4 inhibitors1• ;IKKβ inhibitors2• ;Spiroimidazolidinone NPC1L1 inhibitors3• ;Sulfamides4• ;Phosphodiesterase 5 inhibtors5• ;Anti-HIV agents6

Uses

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.

Synthesis

122.12 g (1.00 mol) of nicotinamide was dissolved in 500 mL of 2-propanol. To this solution was added 14.4 g of 10% palladium-carbon catalyst, followed by stirring the reaction for 4 hours at 75 °C under 0.5 MPa hydrogen pressure. Upon completion of the reaction, the palladium-carbon catalyst was removed by filtration and the filter cake was washed with 100 mL of 2-propanol. The filtrate and washings were combined and concentrated to give 126.08 g of racemic 3-piperidinecarboxamide white crystals in 98.4% yield. The structure of the product was confirmed by NMR characterization.

References

[1] Patent: US2012/123128, 2012, A1. Location in patent: Page/Page column 3
[2] Synlett, 2006, # 9, p. 1440 - 1442
[3] Chemistry - A European Journal, 2009, vol. 15, # 28, p. 6953 - 6963
[4] Synlett, 2008, # 8, p. 1125 - 1128
[5] Journal of the American Chemical Society, 1949, vol. 71, p. 1680

NIPECOTAMIDE(4138-26-5)Related Product Information

• Dihydroergotoxine mesylate
• Umespirone
• (2S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide)
• NIPECOTAMIDE
• Cabergoline
• Rispenzepine
• dihydroergocristine
• N,N-DIETHYLNIPECOTAMIDE
• DIHYDROERGOCRISTINE MESYLATE
• Epicriptine
• amesergide
• DIHYDROERGOTAMINE TARTRATE
• 1-methylpiperidine-3-carboxamide (HCl)
• (R)-1-N-BOC-PIPECOLAMIDE
• LONAFARNIB
• Pipecolamide
• Mepivacaine hydrochloride
• Dihydroergotoxine