Synthetic Route of 5003-71-4,Some common heterocyclic compound, 5003-71-4, name is 3-Bromopropan-1-amine hydrobromide, molecular formula is C3H9Br2N, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Step A N-Benzyloxycarbonyl-3-bromopropylamine To a stirred suspension of 3-bromopropylamine hydrobromide (2 g, 9.14 mM) in 40 mL dry THF was added, via hypodermic syringe, benzyl chloroformate (1.64 g, 9.60 mM) at room temperature. After cooling to 0 C., diisopropylethylamine (1.6 mL, 9.20 mM) was added dropwise via syringe and the reaction mixture was allowed to stir at 0 C. for 1 hour. The crude reaction mixture was filtered over a pad of Celite and solvents were evaporated. The residue was flash chromatographed on silica gel, eluding with 10-20-30% EtOAc/hexane to afford 1.56 g desired product as a liquid, homogeneous by TLC in 80:20 hexane-EtOAc; 1 H-NMR (200 MHz, CDCl3, ppm) delta2.06 (m, 2H), 3.37 (m, 4H), 4.92 (br, 1H), 5.10 (s, 2H), 7.34 (s, 5H). Mass spectrum (FAB) m/e 273 (M+1)+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromopropan-1-amine hydrobromide, its application will become more common.
Reference:
Patent; Merck & Co., Inc.; US5411980; (1995); A;,
Bromide – Wikipedia,
bromide – Wiktionary