tert-Butyl piperazine-1-carboxylate → HCID 46867019, compound

Participants

Reaction Steps

To a solution of 3-bromomethyl-5-methylisoxazole (0.102 g, 0.58 mmol) in dichloromethane (6 ml) was added 1-BOC-piperazine (0.240 g, 1.30 mmol). The reaction mixture was stirred at room temperature for 18 h under argon, then concentrated in vacuo. The resulting residue was absorbed on silica and the free-running powder was placed on a 10 g isolute silica column. Elution with a gradient of ethyl acetate (30 to 70%) in petroleum ether (60-80° C.) afforded the title compound as a white solid (0.124 g, 76%). 1H-NMR (500 MHz, DMSO-d6) 1.39 (s, 9H, C(CH3)3), 2.32 (t, J=5.1 Hz, 4H, piperazine N(CH2)2), 2.38 (s, 3H, isoxazole 5-CH3), 3.35 (br t, 4H, piperazine N(CH2)2), 3.50 (s, 2H, NCH2 isoxazole), 6.17 (s, 1H, isoxazole 4-H); LC (Method B)-MS (ESI, m/z): Rt=2.60 min—282 [(M+H)+, 5%], 226 [(M-tBu)+, 100%].

Provenance & Evidence