Methylamine → (+/-)-N-methyl-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)ethanamine

Participants

Reaction Steps

A solution of 82 (1.2 g, 4.9 mmol) in 30% methanamine in MeOH (50 mL) was stirred at RT for 15 h. To the reaction mixture was added NaBH4 (186 mg, 4.9 mmol) at RT in several portions and stirred overnight. The reaction mixture was concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (100:1) followed by reverse phase chromatography on CombiFlash® eluting with 0.01% NH4OH ammonia in water (solvent A) and MeCN (solvent B) to afford 200 mg (15%) of (±)-N-methyl-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)ethanamine (84) as yellow oil: MS (ESI) m/z=260.3 (M+1).

Provenance & Evidence