Tetrahydrofuran → Cyclopropyl-{4-[3-(1-cyclopropylpiperidin-4-yl)[1,2,4]oxadiazol-5-yl]phenyl}methanone, Hydrochloride

Participants

Reaction Steps

To a Grignard mixture (prepared from magnesium (50 mg, 2.1 mmol) and cyclopropylbromide (211 mg, 1.7 mmol) in dry THF (2 ml)) placed under an atmosphere of nitrogen was added dropwise a solution of 4-[3-(1-cyclopropylpiperidin-4-yl)[1,2,4]oxadiazol-5-yl]benzonitrile (250 mg, 0.85 mmol, prepared as described in Example 37) in dry THF (1.5 ml). When addition was complete the mixture was heated at reflux for 1 h. The mixture was allowed to cool and then saturated ammonium chloride (1 ml) was added. The mixture was extracted with ethyl acetate (15 ml) and the organic phase was dried (MgSO4) and the solvent was evaporated. The residue was dissolved in a mixture of ethanol (10 ml) and 1 N hydrochloric acid (1 ml) and the solvents were evaporated. The residue was re-evaporated with acetonitril and then stirred with ethyl acetate. This afforded 0.23 g containing the title compound. HPLC: Rt=12.45 min.

Provenance & Evidence