[CH2:1]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)[CH2:2][C:3]#[CH:4].[C:11](Cl)(=[O:22])OC1C=CC([N+]([O-])=O)=CC=1.C[CH2:25][N:26](CC)CC>C1COCC1.O.CO.CN>[CH2:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([NH:26][CH3:25])=[O:22])[CH2:7][CH2:6]1)[CH2:2][C:3]#[CH:4]A solution of 1-(but-3-ynyl)piperazine (445 mg) in THF (4 mL) was treated with 4-nitrophenyl carbonochloridate (649 mg) at rt for 5 min. A precipitate formed immediately, and the suspension was treated with Et3N (0.45 mL) to ensure complete reaction. The suspension was diluted with H2O (2 mL), MeOH (2 mL) and 40% aq. MeNH2 (4.0 mL) and stirred at rt for 3 days. Extraction with DCM (50 mL), washing (NaOH 2M), drying (Na2SO4) and concentration gave 4-(but-3-ynyl)-N-methylpiperazine-1-carboxamide (370 mg).
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