2-Nitro-4-fluoro-5-(piperidin-1-yl)aniline → 4-Fluoro-5-(piperidin-1-yl)-1,2-phenylenediamine

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Reaction Steps

The nitroaniline derivative (6.2 g, 0.026 mol) (obtained in step 1 above) was hydrogenated using 10% Pd-C (1.0 g,) in ethanol (30 mL), using an analogous procedure as described in preparation 1 (step 4) to yield 4-fluoro-5-(piperidin-1-yl)-1,2-phenylenediamine (5.3 g 98%) as brown viscous oil. IR (Neat) 3346 cm-1 ; 1H NMR (CDCl3) δ 1.54 (m, 2H, CH2), 1.70 (m, 4H, (CH2)2), 2.90 (m, 4H, N(CH2)2), 3.10 (brs, 4H, 2×NH2), 6.40 (d, J=8.8 Hz, 1H), 6.48 (d, J=13.8 Hz, 1H); Mass (m/z) 209 (M+.).

Provenance & Evidence