Triethylamine → tert-Butyl 4-((1,2,4-oxadiazol-3-yl)methyl)piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of Boc-piperazine (571 mg, 3.07 mmol) and 3-(chloromethyl)-1,2,4-oxadiazole (400 mg, 3.37 mmol) in CH2Cl2 (30 mL) was added triethylamine (1.70 mL, 12.3 mmol). The reaction was stirred for 22 h at 50° C. before concentrated in vacuo to give a crude oily white solid. Purification was accomplished by flash chromatography on silica gel (4×12) eluting with MeOH/CH2Cl2 (5%) to yield the title compound (555 mg, 67%) as a white solid. 1H-NMR (500 MHz, CDCl3) 1.43 (s, 9H, C(CH3)3), 2.52 (app t, J=4.9 Hz, 4H, CH2), 3.45 (app t, J=4.9 Hz, 4H, CH2), 3.78 (s, 2H, CH2C—), 8.71 (s, 1H, CHar); LC-MS (ESI, m/z): Rt=1.67 min-213 (M-tBu)+, 169 (M-Boc)+.

Provenance & Evidence