1-Phenethylamine → 2-(alpha-Methylbenzylamino) pyrazine

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-phenylethanamine (212 mg, 1.75 mmol) and 2-chloropyrazine (200 mg, 1.75 mmol) in toluene (10 mL) while bubbling N2 was added binap (141 mg, 0.23 mmol), sodium tert-butoxide (235 mg, 2.44 mmol) and palladium(II) acetate (51.0 mg, 0.23 mmol). The reaction mixure was heated at 70 oC for 3 hours. The reaction was concentrated, partitioned between ethyl acetate and water. The aqueous phase was extracted 3 times with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The crude material was loaded on a 40g silica gel column and purified on a Teledyne Isco instrument, eluting with 20% to 70% ethyl acetate in heptane to provide N-(1-phenylethyl)pyrazin-2-amine (148 mg, 42.5 %) as a solid.

Provenance & Evidence