Category: 6781-17-5

Reference of 6781-17-5, A common heterocyclic compound, 6781-17-5, name is 2-(2-Ethoxyphenoxy)ethanamine, molecular formula is C10H15NO2, its 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.

4.87 g of 2-methoxy-5-(2-oxopropyl)benzenesulfonamide, 3.62 g of 2-(2-ethoxyphenoxy)ethylamine and 10 mg of sodium acetate were added to 30 ml of acetonitrile. The mixture was heated while stirred under reflux for about 1 hour. Then, the solvent was evaporated off in vacuo, to give 7.84 g of an imine compound as a powder. The obtained imine compound was again dissolved in 70 ml of acetonitrile, and to this was added 1.0 g of anhydrous magnesium sulfate. The mixture was cooled to -3 to 3C under argon atmosphere. To this mixture was added the whole amount of the above catalyst-containing mixture, and stirring continued at the same temperature for about 30 minutes. To this was added dropwise 12.0 ml of a mixed solution of formic acid/triethylamine (molar ratio: 5/2), and then stirring further continued at the same temperature for about 5 hours. After that, the reaction mixture was gradually returned to room temperature, and stirring continued overnight for completion of the reaction. After that, the solvent was evaporated off in vacuo and the residue was dissolved in methyl isobutyl ketone. Following this, extraction with aqueous methanesulfonic acid solution was performed. After the aqueous layer was rendered weakly alkaline with aqueous sodium hydroxide solution, separated oily material was extracted with methyl ethyl ketone. The extract solution was washed with saturated brine, dried and concentrated, to give 7.96 g of 5-[2-[(2-(2-ethoxyphenoxy)ethyl)amino]propyl]-2-methoxybenzenesulfonamide (crude crystal containing excess R-isomer) as a light brown powder. The obtained compound was analyzed using a chiral chromatography column (CHIRALPAK AD-H; manufactured by Daicel Chemical Industries, Ltd.) with a solvent made of n-hexane/2-propanol/diethylamine (800/200/1). The result showed that the optical purity of the R-isomer was 70.7%ee. Then, 6.0 g of the crude crystal was dissolved in 42.0 ml of aqueous acetone containing 10% water and to this was added 3.36 g of (R)-mandelic acid. The mixture was heat-dissolved, and then allowed to stand at 15 to 25C overnight. The precipitate was collected by filtration, washed with acetone and dried, to give 4.56 g of (R)-tamuslosin (R)-mandelate, i.e., (R)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzenesulfonamide (R)-mandelate as a colorless crystal. The optical purity of the R-isomer of the obtained compound was 97.0%ee. Moreover, recrystallization from aqueous acetone containing 10% water was performed to give 3.29 g of a purified product. The optical purity of the R-isomer of the purified product was 100%ee.Optical rotation: [alpha]D20 -31.90 (C = 0.5, MeOH) NMR: 1H-NMR (200MHz, DMSO-d6): delta 0.99-1.03 (3H, d), 1.23-1.30 (3H, t), 2.47-2.59 (1H, q), 2.97-3.05 (1H, q), 3.10-3.30 (1H, m), 3.14-3.20 (2H, t), 3.88 (3H, s), 3.94-4.04 (2H, q), 4.09-4.15 (2H, t), 4.43 (2H, m), 4.75 (1H, s), 6.82-7.43 (9H, m), 7.04 (2H, m), 7.58-7.60 (1H, d)

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Hamari Chemicals, Ltd.; EP2172443; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 6781-17-5, name is 2-(2-Ethoxyphenoxy)ethanamine, A new synthetic method of this compound is introduced below., Recommanded Product: 2-(2-Ethoxyphenoxy)ethanamine

a) 2-Methoxy-5-(2-oxopropyl)-benzene sulfonamide (37.3 gm, 153.3 mmol), 2-(2-ethoxyphenoxy)-1-ethanamine (29.8 gm, 164.4 mmol) and methanol (250 mL) were taken into a one liter stainless steel flask and mixed well. Catalyst Raney nickel (8 gm) was added to the flask and the mixture hydrogenated at 50 C. at hydrogen pressure of 40 psi for 30 hrs. The catalyst was removed by filtration and solvent from the filtrate was distilled off completely at 50 C. under vacuum. The dark brown crude obtained was treated with methanolic hydrochloric acid (175 mL) at 0-5 C. under stirring. Tamsulosin hydrochloride formed as a solid was filtered, washed with ethyl acetate (200 mL), suspended in methanol (120 mL) and the methanol slurry filtered to obtain off white solid material. It was dried for 3 hrs at 80 C. to give racemic tamsulosin hydrochloride. Melting point 255-257 C., chemical purity of 98.8 area % (by HPLC) and R,S ratio of 51.45:48.55 (by chiral HPLC).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; DIVI’S LABORATORIES LIMITED; US2006/79714; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 6781-17-5, name is 2-(2-Ethoxyphenoxy)ethanamine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 6781-17-5

EXAMPLE 1 A mixture of 1.9 g of 1-chloro-3-(4-fluorophenoxy)-propane, l.8 g of 2-(2-ethoxyphenoxy)ethylamine, 0.53 g of sodium carbonate and 60 ml of dimethylformamide was heated at 80-90 C for 15 hours. After cooling, the reaction mixture was poured into water and extracted with benzene. The extract was washed with water and dried over sodium sulfate and evaporated under reduced pressure. The oily residue was dissolved in ether and treated with ethanolic hydrogen chloride under cooling. The precipitate was collected by filtration and dried to give N-{2-(2-ethoxyphenoxy)ethyl}-3-(4-fluorophenoxy)propylamine hydrochloride, M.P. 78-82 C. Recrystallization from ethanol-benzene gave white crystals, M.P. 84-86 C.

According to the analysis of related databases, 6781-17-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sumitomo Chemical Company, Limited; US4010280; (1977); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

6781-17-5, name is 2-(2-Ethoxyphenoxy)ethanamine, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C10H15NO2

Example 13 (2-Benzenesulfonyl-ethyl)-[2-(2-ethoxy-phenoxy)-ethyl]-amine hydrochloride A mixture of 2-(2-ethoxyphenoxy)ethanamine (36.2 g, 200 mmol) and [(2-phenoxyethyl)sulfonyl]-benzene (52.5 g, 200 mmol) in 500 mL of tetrahydrofuran is treated in portions with 50% sodium hydride in mineral oil suspension (9.7 g, 202 mmol). The mixture is stirred at room temperature for 1 hour and then evaporated. The residue is partitioned between ethyl ether and brine. The ether layer is dried (anhydrous magnesium sulfate) and treated with hydrogen chloride gas. The precipitated solid is filtered and recrystallized from ethanol to give 49.6 g (64%) of product, mp 146-152 C.

The synthetic route of 6781-17-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US6051605; (2000); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 6781-17-5, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 6781-17-5, name is 2-(2-Ethoxyphenoxy)ethanamine, This compound has unique chemical properties. The synthetic route is as follows.

(a) Synthesis of Oxalate Salt of Racemic Tamsulosin 2-(o-Ethoxyphenoxy)ethylamine (45 gm) was dissolved in methanol (250 mL). To this 2-methoxy-5-(2-oxopropyl)-benzene sulfonamide (55 gm), catalyst 5% platinum on carbon (12.1 gm) and methanol (330 mL) were added. The mixture was hydrogenated in autocalve at 55 C. at hydrogen pressure of 13 kg/cm2 for 5 hrs. The reaction mixture was cooled and the catalyst was filtered off. To the filtrate containing racemic tamsulosin, oxalic acid (14.3 gm) was added and the solvent was distilled off. To the residue, acetone (700 mL) was added and stirred at reflux temperature for 30 mins. The mixture was cooled, filtered, and the filter cake washed with acetone (50 mL). The salt was further purified by suspending the material in 2-propanol at reflux temperature, cooling to ambient temperature and filtering the solid. The pure oxalate salt of racemic tamsulosin shows a melting range of: 178-182 C. and HPLC purity: 97.24 (area %). The chiral HPLC showed it to be a mixture R and S isomers in the ratio of 50.1 to 49.9. The infrared spectrum of the oxalate salt of racemic tamsulosin as shown in of the drawing accompanying this specification, exhibited peaks at cm-1: 1154 & 1332 (SO2), 3408 (-NH2), 2983 (NH2+), 1591 (COO-). The 1H-NMR spectrum in CD3SOCD3 gave signals at 8 values: 1.06-1.08 (3H, d, >CH-), 1.30-1.33 (3H, t, -CH2-), 3.89 (3H, s, -O), 4.15-4.36 (10 H, 4-CH2, -CH, -NH), 7.61 (2H, s, -NH2), 6.8-7.5 (7H, m, Ar-H). The 13C-NMR spectrum exhibited signals as expected, in particular at delta values 56.34 (-OH3), 14.93 (-OCH2H3), 17.29 (-CH.H3), 54.59 (-H.CH3), 64.11 (-OH2.CH3), 44.51 (-NH.H2.CH2.CH2.O-), 67.25 (-NH.CH2.H2.O-), 39.53 (-H2.CH-), 165.35 (COOH oxalate). Element analysis: C=53.64% (Calcd. 53.49%), H=6.57% (Calcd. 6.62%), N=5.89% (Calcd. 5.95%) and S=6.58% (Calcd. 6.79%) and corresponds to the hydrate, M.Wt. 471.53, C21H29N2O7S.H2O. The ES-mass spectrum signal at m/z=409 corresponded to mass of free base. The XRD trace shows strong peaks at 2 theta values: 20.36, 22.33, 14.8, and 13.74 in that sequence as shown in . The DSC thermogram of pure salt exhibited a sharp peak at 180.2 C. as shown in

The chemical industry reduces the impact on the environment during synthesis 2-(2-Ethoxyphenoxy)ethanamine. I believe this compound will play a more active role in future production and life.

Application of 6781-17-5, 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. 6781-17-5, name is 2-(2-Ethoxyphenoxy)ethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 14 (3-Benzenesulfonyl-propyl)-[2-(2-ethoxy-phenoxy)-ethyl]-amine oxalate A mixture of [(3-bromopropyl)sulfonyl]benzene (26.3 g, 100 mmol), 2-(2-ethoxyphenoxy)ethanamine (18.1 g, 100 mmol), and potassium carbonate (55.3 g, 400 mmol) in 200 mL of methyl ethyl ketone is heated at reflux for 18 hours. The reaction mixture is cooled, filtered, and the filtrate is evaporated. The residue is dissolved in warm 2-propanol and treated with oxalic acid (9.3 g, 101 mmol). The precipitated salt is filtered and recrystallized from 2-propanol to yield 3.2 g (7%) of product, mp 184-188 C.

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-(2-Ethoxyphenoxy)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Warner-Lambert Company; US6051605; (2000); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem