Ammonium Chloride → 1-(2-piperidin-1-yl-ethyl)-1H-indazol-4-ylamine

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Reaction Steps

A mixture of 4-Nitro-1-(2-piperidin-1-yl-ethyl)-1H-indazole (mmol), iron powder (mmol), and ammonium chloride (mmol) in a 4:1 solution of ethanol/H2O was heated to reflux for 2 hours, cooled to room temperature and concentrated under reduced pressure. The residue was stirred in triethylamine/ethyl acetate (1/4, 30 mL) for 15 minutes and filtered through a plug of silica gel which was rinsed with triethylamine/ethyl acetate (1/4). The filtrate was concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm 1.36 (m, 2 H), 1.44 (m, 4 H), 2.37 (m, 4 H), 2.66 (t, J=6.95 Hz, 2 H), 4.33 (t, J=6.95 Hz, 2 H), 5.71 (m, 2 H), 6.12 (m, 1 H), 6.66 (m, 1 H), 6.99 (m, 1 H), 8.02 (m, 1 H); MS (DCI/NH3) m/z 245 [M+H]+.

Provenance & Evidence