Hydrochloric Acid → 1-(p-Tolyl)cyclopropanamine

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of p-tolunitrile (1195 mg, 10.00 mmol) in dry Et2O (50 mL) was treated at −78° C. with Ti(Oi-Pr)4 (3.22 mL, 11.00 mmol) followed by EtMgBr (7.33 mL of a 3.0 M solution in Et2O, 22.00 mmol). The resulting yellow suspension was stirred at −78° C. for 10 min, then warmed up to rt. To the resulting black suspension was added BF3.Et2O (2.47 mL, 20.00 mmol) and the reaction mixture was stirred at rt for 1 h. Aqueous 1N HCl (30 mL) was carefully added, followed by Et2O and then 10% aqueous NaOH (100 mL). The layers were separated and the aq. layer extracted with Et2O. The combined org. extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by FC(CH2Cl2/MeOH/NH4OH, 1:0:0→90:10:0.5) to get the title amine as a yellow oil. TLC: rf (CH2Cl2/MeOH/NH4OH, 95:5:0.5)=0.46. LC-MS-conditions 07b: tR=0.49 min; [M+H]+=148.29.

Provenance & Evidence