Benzonitrile → 1-Phenyl-cyclopropylamine

Participants

Reaction Steps

To a solution of benzonitrile (1.03 g, 10 mmol) in DCM (50 mL) at −60° C. was added Ti(OiPr)4 (3.22 mL, 11 mmol) and EtMgBr (3M in ether, 7.34 mL, 22 mmol), the resulting dark brown solution was slowly warmed up to room temperature over 1 h. BF3.OEt2 (2.47 mL, 20 mmol) was added, and the solution was further stirred at room temperature for 2 h. The mixture was quenched with Sat. NH4Cl and 1N HCl, aqueous layer was separated and extracted with ether, and then neutralized with 5N NaOH to pH=10. The resulting precipitate was filtered off and the filtrate was extracted with EtOAc, EtOAc layer was combined, dried and concentrated to give 1-phenylcyclopropanamine as oil (600 mg).

Provenance & Evidence