3-Bromopropylamine hydrobromide → 5-Phenyl-penta-2,4-dienoic acid (3-bromo-propyl)-amide

Beteiligte Stoffe

Reaktionsschritte

To a suspension of 3-bromopropylamine hydrobromide (1.09 g, 5.0 mmol) in anhydrous methylene chloride triethylamine (0.61 g, 6.0 mmol) was added and the mixture was stirred at ambient temperature for 30 min. The mixture was cooled in the ice bath and a solution of 5-phenyl-penta-2,4-dienoic acid 2,5-dioxo-pyrrolidin-1-yl ester (10) (1.35 g, 5.0 mol) in methylene chloride (20 ml) was added. The reaction mixture was stirred at ice bath temperature for 1.5 hours and at ambient temperature for 2 hours. The solvent was removed and the residue was suspended in water. The precipitate was filtered and washed with water and hexane to give the title compound 11 (1.0 g, 68%). 1H NMR (CDCl3, HMDSO) δ: 1.92-2.32 (2H, m); 3.31-3.67 (4H, m); 6.00 (1H, d, J=15.0 Hz); 6.07 (1H, br s); 6.78-6.96 (2H, m); 7.22-7.61 (6H, m).

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