ChemicalBook CAS DataBase List 1-(2-MORPHOLIN-4-YLETHYL)-1H-BENZIMIDAZOL-2-AMINE

1-(2-MORPHOLIN-4-YLETHYL)-1H-BENZIMIDAZOL-2-AMINE synthesis

6synthesis methods

Product Name:1-(2-MORPHOLIN-4-YLETHYL)-1H-BENZIMIDAZOL-2-AMINE
CAS Number:26840-48-2
Molecular formula:C13H18N4O
Molecular Weight:246.31

934-32-7 Synthesis

934-32-7
323 suppliers
$6.00/5g

3647-69-6 Synthesis

4-(2-Chloroethyl)morpholine hydrochloride

3647-69-6
355 suppliers
$5.00/10g

1-(2-MORPHOLIN-4-YLETHYL)-1H-BENZIMIDAZOL-2-AMINE

26840-48-2
15 suppliers
$318.00/1g

Yield:26840-48-2 65%

Reaction Conditions:

with potassium carbonate;potassium hydroxide in acetone; for 3 h;Reflux;

Steps:

6.1.1.1 Method A (compounds 8a-f,l-o)

General procedure: A mixture of 2-aminobenzimidazole 7 (1.33 g, 10.0 mmol), 10.0 mmol of the proper alkyl halide, 1.0 g of finely powdered KOH mixed with 2.0 g of anhydrous K₂CO₃ and acetone (50 mL) was heated at reflux for 3 h, with stirring. The solvent was removed in vacuo and the residue was partitioned between water (100 mL) and CH₂Cl₂ (100 mL), and the aqueous phase was further extracted twice with CH₂Cl₂. The combined extracts, dried over anhydrous Na₂SO₄, after removal of solvent afforded an oily or solid residue which was treated with a small amount of ethyl ether to give compounds 8a-e,l-o as whitish solids which were crystallized from the proper solvent. Only in the case of compound 8f, a preliminary purification by column chromatography [SiO₂/ethyl acetate-acetone (1:1)] was necessary to obtain a crystalline compound.

References:

Di Braccio, Mario;Grossi, Giancarlo;Signorello, Maria Grazia;Leoncini, Giuliana;Cichero, Elena;Fossa, Paola;Alfei, Silvana;Damonte, Gianluca [European Journal of Medicinal Chemistry,2013,vol. 62,p. 564 - 578]