Aluminium lithium hydride → HCID 178420861, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (1H-benzoimidazol-5-yl)-morpholin-4-yl-methanone (1 g, 4.32 mmol) in THF (60 mL) at 0° C. was added LiAlH4 (2M in THF; 4.32 mL, 8.65 mmol) dropwise. The mixture was stirred 0° C. for 2 hours then warmed to room temperature for 2 hours. The mixture was cooled again to 0° C. and then quenched by addition of H2O (0.328 mL), followed by 15% aqueous NaOH solution (0.328 mL) and finally H2O (3×0.328 mL). The mixture was stirred for 1 hour and left to stand overnight. The mixture was diluted with THF, filtered, concentrated in vacuo and purified by SiO2 chromatography to give 5-morpholin-4-ylmethyl-1H-benzoimidazole (838 mg). Step 3 was performed by repeating procedures described for Example 1 then gave the title compound as a mixture of two regioisomers.

Provenance & Evidence