Tetrahydrofuran → 1,1-Dimethylethyl 4-(4-amino-3-methylphenyl)-1-piperazinecarboxylate

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Reaction Conditions

Reaction Steps

tert-Butyl 4-(3-methyl-4-nitrophenyl)piperazine-1-carboxylate (1.25 g, 3.90 mmoles), 1 equivalent), tetrahydrofuran (10 ml), water (10 ml), iron dust (1.09 g, 19.5 mmoles, 5 equivalents), and ammonium formate (1.23 g, 19.5 mmoles, 5 equivalents) were combined and heated, with stirring to 75° C. for 12 hours (overnight). The hot mixture was filtered through a plug of Celite and washed with ethyl acetate. The filtrate was evaporated under reduced pressure and extracted with ethyl acetate. The ethyl acetate solution was washed with water and saturated sodium chloride solution. The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give 1.11 g of tert-butyl 4-(4-amino-3-methylphenyl)piperazine-1-carboxylate. 1H-NMR (400 MHz, CDCl3), δ 6.47 (d, 1H), 6.16 (d, 1H), 6.14 (d, 1H), 5.85 (bs, 2H), 3.35 (m, 4H), 3.19 (m, 4H), 2.35 (s, 3H), 1.42 (s, 9H). MS (EI) for C16H25N3O2, 292 (MH+).

Provenance & Evidence