tert-Butyl piperazine-1-carboxylate → HCID 57897266, compound

Participants

Reaction Steps

To a stirred solution of 2-bromo-N-(3-methylisoxazol-5-yl)acetamide (0.122 g, 0.58 mmol) in anhydrous dichoromethane (4.5 ml) under argon was added 1-BOC-piperazine (0.241 g, 1.30 mmol). The reaction mixture was stirred at room temperature for 2 h under argon, then partitioned between ethyl acetate (100 ml) and 6% aqueous Na2CO3 (50 ml). The organic layer was washed with more 6% aqueous Na2CO3 (50 ml), and concentrated in vacuo. The residue was absorbed on silica gel and the free-running powder was placed on a 10 g isolute column. Elution of the column with 30% ethyl acetate in dichloromethane afforded the title compound as a white solid (0.096 g, 51%). 1H-NMR (500 MHz, DMSO-d6) 1.39 (s, 9H, C(CH3)3), 2.18 (s, 3H, CH3), 2.45 (t, J=5.1 Hz, 4H, piperazine N(CH2)2), 3.23 (s, 2H, NCH2CO), 3.34 (t, J=4.7 Hz, 4H, piperazine N(CH2)2), 6.13 (s, 1H, isoxazole C—H), 11.28 (s, 1H, CONH);

Provenance & Evidence