Hydrazine hydrate (1:1) → 1,1-Dimethylethyl 4-[(5-amino-7-benzofuranyl)methyl]-1-piperazinecarboxylate

Participants

Reaction Steps

Raney nickel (slurry in ethanol) and hydrazine hydrate (66 μL, 1.36 mmol) were added to tert-butyl 4-[(5-nitro-1-benzofuran-7-yl)methyl]piperazine-1-carboxylate (123 mg, 0.34 mmol; obtained in Step 1) in ethanol:THF (4:1; 10 mL). The mixture was stirred at room temperature for 1 h. Unreacted starting material was still present and additional Raney nickel and hydrazine hydrate (33 μL, 0.68 mmol) were added with continuos stirring for 1 h. The mixture was filtered through a pad of Celite, which was rinsed several times with ethanol. Evaporation of the solvent gave 119 mg (quantitative) of the title amine as a green sticky oil which was used directly in the next step.

Provenance & Evidence