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

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).

1. additionwas added
2. stirringThe reaction mixture was stirred at ice bath temperature for 1.5 hours
3. waitat ambient temperature for 2 hours
4. customThe solvent was removed
5. filtrationThe precipitate was filtered
6. washwashed with water and hexane

ORD record

ord-4f6ed78d6d93485c82284bf22c56709f

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06960685B2