Ammonium Chloride → HCID 71272570, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)ethanone oxime (1.1 g, 4.0 mmol), zinc (2.6 g, 40.0 mmol) and NH4Cl (2.2 g, 40.0 mmol) in MeOH (20 mL) and HOAc (4 mL) was stirred at 80° C. for 4 h. The reaction mixture was filtered and the filtrate concentrated in vacuo. Aqueous ammonia solution (50 mL) was added to the residue, and the mixture was extracted with DCM (50 mL×3), dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH/TEA (10:1:0.2) to afford 1-(6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)ethanamine (101) as a yellow solid (840 mg, 80%). MS (ESI): m/z=260.2 [M+1]+.

Provenance & Evidence