Aluminium lithium hydride → 3-{4-[3-(1-Methyl-1H-benzoimidazol-2-yl)-phenyl]-piperazin-1-ylmethyl}-morpholine-4-carboxylic acid tert-butyl ester

To a solution of 3-{4-[3-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperazine-1-carbonyl}-morpholine-4-carboxylic acid tert-butyl ester (0.21 g, 0.42 mmol) in dry THF (3 mL) at room temperature under a nitrogen atmosphere was added lithium aluminium hydride (LiAlH4) (0.05 g, 1.27 mmol). The reaction was heated at reflux for 2 h. The solution was then cooled to room temperature, quenched with 15% NaOH and then extracted with dichloromethane (3×10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude was then purified by Preparative HPLC to obtain 0.09 g (43%) of the title compound.