Category: 10578-75-3

Application of 10578-75-3,Some common heterocyclic compound, 10578-75-3, name is 2-(Benzyloxy)ethanamine hydrochloride, molecular formula is C9H14ClNO, 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.

2,4-Dichloro-6,7-dimethyl-3-nitropyridine (26.89 g, 121.7 mmol), anhydrous N,N-dimethylformamide (400 mL), anhydrous triethylamine (48.84 mL), and the benzyloxyethylamine hydrochloride salt (27.4 g, 146.0 mmol) from Part B were combined under nitrogen and heated to 90 C. for 20 minutes, 60 C for 1 hour, and then 90 C. for 1 hour. The reaction was complete as determined by TLC analysis using 8/2 hexane/ethyl acetate. The reaction mixture was concentrated under reduced pressure, and the resulting orange solids were triturated with water. The resulting solids were filtered off and recrystallized from ethyl acetate. Recrystallized solids were rinsed with hexane and dried under vacuum at 50 C. for 30 minutes to provide 21.8 g of yellow fluffy solid for use in the next step. NMR analysis confirmed the N-[2-(benzyloxy)ethyl]-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine and a minor amount of residual salts.; Under a nitrogen atmosphere, triethylamine (40.4 mL, 290 mmol) was added to a solution of 2,4-dichloro-6-methyl-3-nitropyridine (12.0 g, 58.0 mmol), prepared according to the general method of Part A of Example 1 using 2,4-dihydroxy-6-methyl-3-nitropyridine in lieu of 2,4-dihydroxy-5,6-dimethyl-3-nitropyridine, in anhydrous N,N-dimethylformamide (DMF) (200 mL). To the resulting dark brown solution was added 2-(benzyloxy)ethylamine hydrochloride (11.97 g, 63.76 mmol), and the mixture was stirred at room temperature for 23 hours. The volatiles were then removed under reduced pressure, and the residue was mixed with water and ethyl acetate. The organic layer was washed with water (3×200 mL), aqueous sodium bicarbonate (2×200 mL), and brine (3×250 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide a brown oil. The crude product (18.1 g) was purified by column chromatography on silica gel (700 g, eluting with 80:20 hexane:ethyl acetate) to provide an oil which was triturated with 80:20 hexane:ethyl acetate. The resulting crystals were isolated by filtration and dried to provide 4.7 g of [2-(benzyloxy)ethyl]-(2-chloro-6-methyl-3-nitropyridin-4-yl)amine as a yellow solid.

The synthetic route of 10578-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dellaria, Joseph F.; Lindstrom, Kyle J.; Dressel, Luke T.; Duffy, Daniel E.; Heppner, Philip D.; Jacobsen, John R.; Moseman, Joan T.; Moser, William H.; Radmer, Matthew R.; Stoermer, Doris; Zimmermann, Bernhard M.; US2004/10007; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

10578-75-3, A common compound: 10578-75-3, name is 2-(Benzyloxy)ethanamine hydrochloride, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

2,4-Dichloro-6,7-dimethyl-3-nitropyridine (26.89 g, 121.7 mmol), anhydrous N,N-dimethylformamide (400 mL), anhydrous triethylamine (48.84 mL), and the benzyloxyethylamine hydrochloride salt (27.4 g, 146.0 mmol) from Part B were combined under nitrogen and heated to 90 C. for 20 minutes, 60 C for 1 hour, and then 90 C. for 1 hour. The reaction was complete as determined by TLC analysis using 8/2 hexane/ethyl acetate. The reaction mixture was concentrated under reduced pressure, and the resulting orange solids were triturated with water. The resulting solids were filtered off and recrystallized from ethyl acetate. Recrystallized solids were rinsed with hexane and dried under vacuum at 50 C. for 30 minutes to provide 21.8 g of yellow fluffy solid for use in the next step. NMR analysis confirmed the N-[2-(benzyloxy)ethyl]-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine and a minor amount of residual salts.; Under a nitrogen atmosphere, triethylamine (40.4 mL, 290 mmol) was added to a solution of 2,4-dichloro-6-methyl-3-nitropyridine (12.0 g, 58.0 mmol), prepared according to the general method of Part A of Example 1 using 2,4-dihydroxy-6-methyl-3-nitropyridine in lieu of 2,4-dihydroxy-5,6-dimethyl-3-nitropyridine, in anhydrous N,N-dimethylformamide (DMF) (200 mL). To the resulting dark brown solution was added 2-(benzyloxy)ethylamine hydrochloride (11.97 g, 63.76 mmol), and the mixture was stirred at room temperature for 23 hours. The volatiles were then removed under reduced pressure, and the residue was mixed with water and ethyl acetate. The organic layer was washed with water (3¡Á200 mL), aqueous sodium bicarbonate (2¡Á200 mL), and brine (3¡Á250 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide a brown oil. The crude product (18.1 g) was purified by column chromatography on silica gel (700 g, eluting with 80:20 hexane:ethyl acetate) to provide an oil which was triturated with 80:20 hexane:ethyl acetate. The resulting crystals were isolated by filtration and dried to provide 4.7 g of [2-(benzyloxy)ethyl]-(2-chloro-6-methyl-3-nitropyridin-4-yl)amine as a yellow solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-(Benzyloxy)ethanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dellaria, Joseph F.; Lindstrom, Kyle J.; Dressel, Luke T.; Duffy, Daniel E.; Heppner, Philip D.; Jacobsen, John R.; Moseman, Joan T.; Moser, William H.; Radmer, Matthew R.; Stoermer, Doris; Zimmermann, Bernhard M.; US2004/10007; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem