Hydrazine hydrate (1:1) → Tert-butyl 4-[(5-amino-1-benzofuran-7-yl)methyl]-3-methylpiperazine-1-carboxylate

Participants

Reaction Steps

Raney nickel (slurry in ethanol) and hydrazine hydrate (97 μL, 2.0 mmol) were added to tert-butyl 3-methyl-4-[(5-nitro-1-benzofuran-7-yl)methyl]piperazine-1-carboxylate (115 mg, 0.31 mmol; obtained in Step 1) in ethanol:THF (4:1; 5 mL). The resulting mixture was stirred at room temperature for 1.5 h, followed by filtration through Celite. The Celite pad was rinsed several times with ethanol. The solvent was evaporated to give the crude product (136 mg) as a light green solid. This material was used in the next step without further purification. HPLC 98%, RT=1.77 min (System A; 5-60% MeCN over 3 min), 100%, RT=1.50 min (System B; 5-60% MeCN over 3 min). MS (ESI+) for C19H27N3O3 m/z 346 (M+H)+.

Provenance & Evidence