1-Chloro-2,4-Dinitrobenzene → HCID 59799760, compound

Participants

Reaction Conditions

Reaction Steps

Chloro-2,4-dinitrobenzene 1 (2.0 g, 9.874 mmol) was dissolved in anhydrous EtOH (40 mL) in a small argon purged flask and warmed in an oil bath to 40° C. Addition of 1-Methyl-piperidin-4-ylamine 50 (1.24 g, 10.862 mmol) occurred dropwise. The solution was heated to reflux in an oil bath for 48 hours. After cooling to room temperature the solvent was removed under reduced pressure and the resulting residue partitioned between H2O and ethyl acetate and IM ammonium hydroxide solution added to adjust pH to 9. The mixture was transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were washed with H2O, brine (twice), dried over magnesium sulphate, filtered and then concentrated. Recrystallization of the crude solid from EtOH yielded a yellow solid 51 (2,4-Dinitro-phenyl)-(1-methyl-piperidin-4-yl)-amine Yield: 1.50 grams (54.2%). 1H NMR (DMSO) δ: 1.59-1.75 (m, 2H), 1.86-1.98 (m, 2H), 2.06-2.17 (m, 2H), 2.18 (s, 3H), 2.62-2.77 (m, 2H), 3.71-3.84 (m, 1H), 7.31 (d, 1H, J=9.7), 8.24 (dd, 1H, J=9.7, 2.7), 8.45 (d, 1H, J=7.7), 8.85 (d, 1H, J=2.6); MS (ESI): 281 (MH+, 100%).

Provenance & Evidence