2-PIPERIDIN-4-YL-1H-BENZOIMIDAZOLE Chemical Properties

Melting point:

230 °C (decomp)(Solv: water (7732-18-5))

Boiling point:

441.3±38.0 °C(Predicted)

Density 

1.167±0.06 g/cm3(Predicted)

vapor pressure 

0Pa at 25℃

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

Solid

pka

11.83±0.10(Predicted)

color 

White to Light yellow to Light orange

λmax

279nm(MeOH)(lit.)

InChI

InChI=1S/C12H15N3/c1-2-4-11-10(3-1)14-12(15-11)9-5-7-13-8-6-9/h1-4,9,13H,5-8H2,(H,14,15)

InChIKey

HBOGHPAOOWUTLB-UHFFFAOYSA-N

SMILES

C1(C2CCNCC2)NC2=CC=CC=C2N=1

Safety Information

Hazard Codes 

Xi

HS Code 

2933.99.8290

HazardClass 

IRRITANT

2-PIPERIDIN-4-YL-1H-BENZOIMIDAZOLE Usage And Synthesis

Chemical Properties

2-(4-piperidinyl)-1H-benzimidazole is white or brownish-yellow solid under normal temperature and pressure, with good solubility in methanol.

Uses

2-Piperidin-4-yl-1H-benzimidazole is used as a reagent in the synthesis of 3-amino-1-(5-indanyloxy)-2-propanol derivatives as potent sodium channel blockers for the treatment of ischemic stroke. Also used as a reagent in the synthesis of 2,3,5-trisubstituted pyridine derivatives as potent Akt1/Akt2 dual inhibitors.

Synthesis

The general procedure for the synthesis of 2-(4-piperidinyl)-1H-benzimidazole from 4-piperidinecarboxylic acid and o-phenylenediamine was as follows: according to the method described in the literature (J. Heterocyclic Chem., 1989, 26, 54), benzene-1,2-diamine (12.6 g, 116 mmol) was mixed with piperidine-4-carboxylic acid (15 g, 116 mmol) in a 4M HCl aqueous solution (250 mL), stirred and heated under reflux conditions for 48 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted to alkaline with 5 M NaOH aqueous solution. The precipitate precipitated was collected by filtration, washed with water and subsequently dried in a vacuum oven to afford the target product 2-(piperidin-4-yl)-1H-benzimidazole 8.8 g in 38% yield. Mass spectrometry analysis showed m/z = 202 [M+ + H].

References

[1] Patent: US6660751, 2003, B1. Location in patent: Page column 7,8
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 3, p. 695 - 699
[3] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 3, p. 707 - 718
[4] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 541 - 543
[5] Patent: WO2010/80357, 2010, A1. Location in patent: Page/Page column 41-42

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