Hydrazine → HCID 74931736, compound

Participants

Reaction Steps

To a solution of racemic(2′R, 3R, 4′S)-6-chloro-2′-[5-chloro-2-(4-nitro-phenoxy)-phenyl]-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.31 g, 0.51 mmol) in anhydrous ethanol (20 mL) was added Raney-Ni (0.6 g) and anhydrous hydrazine (0.118 g, 2.54 mmol). The reaction mixture was stirred at room temperature for 0.5 h, then filtered through a short pad of celite. The filtrate was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate three times. The organic layers were combined, washed with water, brine, and dried over MgSO4, and concentrated to give racemic(2′R, 3R, 4′S)-2′-[2-(4-amino-phenoxy)-5-chloro-phenyl]-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.28 g, 95%).

Provenance & Evidence