Dimethyl Sulfide → 2-{3-[4-Cyclopropylmethyl-piperazin-1-yl]-phenyl}-1-methyl-1H-benzoimidazole

Participants

Reaction Steps

To a solution of cyclopropyl-{4-[3-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperazin-1-yl}-methanone (0.17 g, 0.47 mmol) in dry THF (3.50 mL) was added (CH3)2S.BH3 in THF (0.11 mL, 1.18 mmol) and the resulting suspension was heated at 65° C. overnight. The reaction solution was then cooled to room temperature, solvent was removed under reduced pressure and 1N HCl (3 mL) was added to the residue before heating at 100° C. for 6 h. The reaction was cooled to room temperature, then made basic by the dropwise addition of 15% NaOH and extracted with EtOAc (3×10 mL) The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to afford a residue that was purified by Preparative HPLC, to obtain 0.05 g (32%) of the title compound.

Provenance & Evidence