Propargyl alcohol → 3-[3-(Aminomethyl)phenyl]-2-propyn-1-ol

Participants

Reaction Steps

Cuprous iodide (1.06 mg, 0.0056 mmol) was added to a mixture of (PPh3)2PdCl2 (7.84 mg, 0.011 mmol) and 3-iodobenzylamine (262 mg, 1.12 mmol) in dry diethylamine (7 mL) under a nitrogen atmosphere. Then a solution of propargyl alcohol (41.2 μL, 0.73 mmol) in dry diethylamine (3 mL) was added. The resulting solution was stirred at room temperature for 3 h. The solvent was concentrated in vacuo and the residue was partitioned between water (20 mL) and CHCl3 (20 mL). The aqueous phase was separated and extracted with CHCl3 (20 mL×2). The combined organic phases were dried over Na2SO4, filtered and concentrated. The residue was purified by PTLC (chloroform/methanol 9:1) to give 72 (106 mg, 90% yield). 1H NMR (CDCl3, 300 MHz) δ 7.39-7.26 (m, 4H), 4.48 (s, 2H), 3.85 (s, 2H), 1.73 (br s,22H). MS (m/e) (positive FAB) 162.1 (M+H)+.

Provenance & Evidence