Ammonia → (4-Methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanamine

Participants

Reaction Steps

A 1 L autoclave was cooled under a stream of nitrogen and charged with 4-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde oxime (14.50 g, 0.052 mol, 1.0 equiv.) and aqueous ammonia (30 mL) in MeOH (300 mL). To this was added Raney Nickel (15.0 g, w/w) and the reaction was stirred at RT under hydrogen (pressure ˜60 psi) overnight. The reaction mixture was then filtered through a Celite® pad and the filtrate was concentrated in vacuo. The crude material was purified by neutral alumina column chromatography using a MeOH/DCM gradient (5 to 10% MeOH to afford (4-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanamine (97, 8.0 g, 57%) as a brown viscous oily liquid.

Provenance & Evidence