Share a compound : 5003-71-4

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5003-71-4, name is 3-Bromopropan-1-amine hydrobromide belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 3-Bromopropan-1-amine hydrobromide

To 3-bromopropylamine hydrobromide (139.32 g, 636.40 mmol) was added a solution of di-tert-butyl dicarbonate (112.46 g, 510.13 mmol) in MIBK (800 mL) and 2.5 M sodium hydroxide (310 mL). The resulting mixture was stirred for 1 hour at room temperature. The reaction was monitored by TLC (9:1 isohexane: ethyl acetate, potassium permanganate stain). Water (345 mL) was added and the mixture stirred for 10 minutes. The phases were separated and the lower (aqueous) phase discarded. To the retained organic phase was added 3-benzyl-9- oxa-3,7-diazabicyclo[3.3.1]nonane dihydrochloride (148.43 g, 509.68 mmol; .; see WO 02/083690) and 2.5 M sodium hydroxide (660 mL). This mixture was heated at 65C for 7 hours. At 650C, the phases were separated and the lower (aqueous) phase discarded. The organic phase was re-heated to 650C and extracted with 10% w/w aqueous citric acid (562 mL). The phases were separated and the upper (organic) phase discarded. To the resulting aqueous phase was added MIBK (800 mL) and 5 M sodium hydroxide (230 mL) containing approximately 10% w/v EPO sodium chloride (22.84 g). The resulting mixture was stirred at room temperature for 15 minutes. The phases were separated and the lower (aqueous) phase discarded. The organic phase was azeo-dried by removal of solvent (300 mL) by distillation under reduced pressure (keeping the temperature below 7O0C). The mixture was clarified by filtration whilst still hot and the residue washed with MIBK (115 mL). The temperature was adjusted to 6O0C and a solution of purified (see J. Am. Pharm. Assoc. 239-241 (1949)) 4-chlorobenzenesulfonic acid (99.24 g, 515.20 mrnol) in MIBK (225 mL) was added over 90 minutes. The reaction mixture was then cooled to room temperature causing the product to crystallize from solution. The mixture was cooled to 5C, the product was collected by filtration and the cake washed with MIBK (225 mL). The product was dried as far as possible on the filter, then oven dried in vacuo (50C, 24 h) to give the title compound as a white solid (257.44 g, 453.13 mmol, 89%). 1H NMR (300 MHz, DMSO-d6) delta 7.61 (d, J= 8.7 Hz, 2H), 7.46 – 7.35 (m, 7H), 7.10 (t, J= 5.7 Hz, IH), 4.15 (s, 2H), 3.70 (s, 2H), 3.40 (d, J= 12.1 Hz, 3H), 3.07 (d, J= 11.9 Hz, 4H), 2.97 (q, J= 6.3 Hz, 2H), 2.84 (t, J= 7.1 Hz, 2H), 2.76 (d, J= 11.9 Hz, 2H), 1.70 (quintet, J= 6.7 Hz, 2H), 1.45 (s, 9H).

The synthetic route of 5003-71-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2006/137770; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary