Potassium Carbonate → Tert-butyl 4-(cyanomethyl)piperazine-1-carboxylate

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Reaction Steps

To a stirred solution of 2.7 g (15 mmol) of tert-butyl piperazine-1-carboxylate in 30 mL of anhydrous N,N-dimethylformamide was added 2.4 g (17 mmol) of potassium carbonate followed by 2.1 g (17 mmol) of bromoacetonitrile. The resulting heterogeneous mixture was stirred at ambient temperature of 12 h, quenched with water then extracted with ethyl acetate. The combined organic layers were washed with water then brine, dried over magnesium sulfate and evaporated to dryness in vacuo. The residue was purified by silica gel chromatography eluting with a 0-75% acetone in hexanes gradient to afford the title compound as clear gum (1.0 g, 30%). 1H-NMR (500 MHz, CDCl3) δ 3.53 (s, 2H), 3.48 (t, J=5.0 Hz, 4H), 2.53 (t, J=5.0 Hz, 4H), 1.45 (s, 9H). LC-MS: m/z (ES) 226.2 (MH)+.

Provenance & Evidence