Hydrazine hydrate (1:1) → 4-[4-(1-Methylethyl)-1-piperazinyl]-2,5-bis(methyloxy)aniline

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Reaction Steps

A solution of 1-[2,5-bis(methyloxy)-4-nitrophenyl]-4-(1-methylethyl)piperazine (3.50 g, 11.3 mmol), FeCl3 (0.550 g, 3.4 mmol), activated carbon (4.0 g), and hydrazine hydrate (3.6 mL, 113 mmol) was heated in methanol (50 mL) for 3 hours. The mixture was filtered over celite and concentrated to give 4-[4-(1-methylethyl)-1-piperazinyl]-2,5-bis(methyloxy)aniline as a grey solid (2.00 g, 7.17 mmol, 63% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.10 (d, J=6.60 Hz, 6 H), 2.72 (s, 5 H), 3.03 (s, 4H), 3.59 (s, 2 H), 3.78 (s, 3 H), 3.79 (s, 3 H), 6.34 (s, 1 H), 6.57 (s, 1 H).

Provenance & Evidence