Acetic Acid → [2-(4-Cyclopropylpiperazin-1-yl)benzooxazol-5-ylmethyl]dimethylamine

Participants

Reaction Steps

To a solution of 2-(4-cyclopropylpiperazin-1-yl)benzooxazole-5-carboxaldehyde (350 mg, 1.29 mmol) and dimethylamine hydrochloride (210 mg, 2.58 mmol) in CH3OH/THF (32 mL, 1:3) was added acetic acid (124 mg, 2.06 mmol), followed by NaCNBH3 (120 mg, 2.06 mmol). The mixture was heated at reflux for 12 h. The volatiles were removed under reduced pressure and the residue was diluted with water (5 mL). The mixture was extracted with CH2Cl2 (3×10 mL) and the combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by the preparative HPLC to give 233 mg (60%) of [2-(4-cyclopropylpiperazin-1-yl)benzooxazol-5-ylmethyl]dimethylamine as a trifluoroacetate salt.

Provenance & Evidence