Category: 6298-96-0

Some common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, molecular formula is C9H13NO, 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. HPLC of Formula: C9H13NO

The solution of 4-oxo-4-(pyridin-2-yl)butanal (326 mg, 2 mmol) in dichloromethane (15 mL) was added NaBH(OAc)3(1.27 g, 6 mmol) and HOAc (20 mg, 0.33 mmol) at -70C. The resulting suspension was stirred at the same temperature for 30 min. The reaction was warmed to 0C and added (5)-l-(4- methoxyphenyl)ethanamine (332 mg, 2.2 mmol). The resulting suspension was stirred at room temperature overnight. The reaction mixture was evaporated and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 1/10) to give the desired product (400 mg, 71 %) as a red solid. H NMR (400 MHz, CDC13) delta 8.42 (s, 1H), 7.58- 7.45 (m, 1H), 7.35 (d, / = 7.2 Hz, 1H), 7.15 (d, / = 7.6 Hz, 2H), 7.02 (s, 1H), 6.68 (d, / = 8.0 Hz, 2H), 3.91 (s, 1H), 3.74-3.71 (m, 4H), 3.09 (s, 1H), 3.62 (d, / = 7.2 Hz, 1H), 2.26-2.15 (m, 1H), 1.99- 1.89 (m, 1H), 1.76 (s, 2H), 1.34 (d, J = 4.8 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6298-96-0, its application will become more common.

Reference:
Patent; SUZHOU YUNXUAN YIYAO KEJI YOUXIAN GONGSI; ZHANG, Xiaohu; ZHENG, Jiyue; MA, Haikuo; (184 pag.)WO2019/60860; (2019); 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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, A new synthetic method of this compound is introduced below., COA of Formula: C9H13NO

B) (4S)-Lambda/-((1 S)-1-r4-(methyloxy)phenyllethyll-3.4-dihvdro-2H-pyranor3.2-lpyridin-4- amine: To a solution of crude 2,3-dihydro-4/-/-pyrano[3,2-]pyridin-4-one (2.43 g) in 1 ,2- dichloroethane was added {(1S)-1-[4-(methyloxy)phenyl]ethyl}amine EPO (2.49 g, 16.5 mmol) and acetic acid (1.4 ml_, 24.5 mmol). The reaction mixture was stirred for 1 hour, then sodium triacetoxyborohydride (5.18 g, 24.4 mmol) was added. The reaction mixture was stirred at room temperature for 16 hours, then diluted with dichloromethane and quenched with saturated aqueous sodium bicarbonate solution. The organic layer was separated and dried over sodium sulfate. Filtration and concentration, followed by flash chromatography (0 to 10% aqueous NH4OH in acetonitrile) provided (4S)- Lambda/-{(1S)-1-[4-(methyloxy)phenyl]ethyl}-3,4-dihydro-2/-/-pyrano[3,2-/j]pyridin-4-amine (1.90 g, 38% two step yield) as a brown oil. 1H NMR (400 MHz, CDCI3) delta 8.15 (dd, J = 3.0, 3.0 Hz, 1 H), 7.35 (d, J = 8.6 Hz, 2 H), 7.07 (d, J = 2.8 Hz, 2 H), 6.86 (d, J = 8.7 Hz, 2 H), 4.19 (ddd, J = 11.0, 7.7, 3.3 Hz, 1 H), 4.07 (q, J = 6.5 Hz, 1 H), 4.00 (ddd, J = 11.1 , 7.3, 3.5 Hz, 1 H), 3.91 (t, J = 5.7 Hz, 1 H), 3.80 (s, 3 H), 2.32 (br, 1 H), 1.70 (m, 2 H), 1.44 (d, J = 6.6 Hz, 3 H).

The synthetic route of 6298-96-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/76131; (2006); A2;,
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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

Synthesis of (S)-(-)-1-(4-hydroxyphenyl)ethylamine hydrobromide (6) A solution of (S)-(-)-1-(4-methoxyphenyl)ethylamine (5, 75 g, 496.7 mmol) in 30% hydrogen bromide in acetic acid (350 mL, Aldrich) in a 1 liter sealed tube was heated at 100-110 C. in an oil bath for 6 hours. The reaction was cooled to room temperature, and nitrogen gas was bubbled into the solution to purge the excess HBr (the HBr was purged into aqueous NaOH). Volatiles were then removed in vacuo to afford the crude phenol amine HBr salt 9 (110 g) as a brown oil, which was used in the next reaction without further purification.

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; Bristol-Myers Squibb Company; US2008/9534; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 6298-96-0, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 6298-96-0 as follows.

A mixture of (1S)-1-(4-methoxyphenyl)ethanamine (7.6 g) and itaconic acid (6.5 g) was stirred at 130 C. for 1 hour. After cooling, chloroform was added to the reaction solution. The organic layer was washed with 1 N hydrochloric acid and saturated saline in this order and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain a stereoisomeric mixture (12.7 g) related to the 3-position of the title compound.

According to the analysis of related databases, 6298-96-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Daiichi Sankyo Company, Limited; Takeda, Yasuyuki; Yoshikawa, Kenji; Kagoshima, Yoshiko; Yamamoto, Yuko; Tanaka, Ryoichi; Tominaga, Yuichi; Kiga, Masaki; Hamada, Yoshito; (132 pag.)US2016/46639; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6298-96-0, COA of Formula: C9H13NO

a) 10.0 g (66.1 mmol) (S)-4-methoxy-alpha-methylbenzylamine are added to 30 mL HBr (30% in AcOH) and stirred at 100 C. for 4 h. The reaction mixture is cooled to r.t. and the solvent is removed in vacuo. The crude product is used without further purification.

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, 1-(4-Methoxyphenyl)ethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; US2014/213568; (2014); 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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 6298-96-0

Example II (S)-4-(1-Amino-ethyl)-phenol hydrobromid To 11.0 g (72.7 mmol) (S)-1-(4-methoxy-phenyl)-ethylamine is added carefully 30 mL HBr (30% in HOAc). The mixture is stirred at 100 C. for 4 h. After cooling down to r.t., the solvent is removed in vacuo and the residue is dried in vacuo. The resulting product is used without further purification. C6H11NO*HBr (M=218.1 g/mol) ESI-MS: 121 [M+H-NH3]+Rt (HPLC): 0.50 min (method A)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 6298-96-0.

Reference:
Patent; FLECK, Martin; NOSSE, Bernd; HEINE, Niklas; ROTH, Gerald Juergen; US2013/158004; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 6298-96-0,Some common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, molecular formula is C9H13NO, 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.

The solid compound A (422 g) obtained in the above step was dissolved in 2.0 L of methanol and 10 L of a reaction flask was added.Lithium hydroxide (26 g) was weighed, dissolved in 2.0 L of pure water, and an aqueous solution of lithium hydroxide was added to the reaction flask. The temperature was controlled at 25-30 C for 1 hour, and the reaction was complete.Add water (4.0L) to the reaction flask, with 1N hydrochloric acid to adjust rhoH- = 2-3, a large number of solid precipitation, the solid material filter out, filter, with 2.9L dichloromethane solid solution Clear, magnetic stirrer slowly stirring.Weigh the s-p-methoxyphenylethylamine (151g), dissolved in 1.0L dichloromethane, the amine solution slowly added to the solution, dropping 40-50 minutes, the temperature control at 18 ~ 22 C, After the dropwise addition, the mixture was allowed to stand for 1 hour, and a large amount of fine granular solid and flocculent solid were precipitated. The granular solid sank into the bottom of the container and the floc floats on the upper part of the solution.After overnight, the supernatant was carefully poured out and the bottom solid was filtered and dried at 35 C under reduced pressure to give compound C, solid: 271 g.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(4-Methoxyphenyl)ethylamine, its application will become more common.

Reference:
Patent; Shanghai Jinhe Bio-pharmaceutical Co., Ltd.; Zhang Weizhong; Wang Quanyong; Cai Zhixia; Xie Bin; Feng Leiyu; Wu Yujuan; Tong Zebin; (12 pag.)CN106632368; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 6298-96-0,Some common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, molecular formula is C9H13NO, 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.

The solid compound A (422 g) obtained in the above step was dissolved in 2.0 L of methanol and 10 L of a reaction flask was added.Lithium hydroxide (26 g) was weighed, dissolved in 2.0 L of pure water, and an aqueous solution of lithium hydroxide was added to the reaction flask. The temperature was controlled at 25-30 C for 1 hour, and the reaction was complete.Add water (4.0L) to the reaction flask, with 1N hydrochloric acid to adjust rhoH- = 2-3, a large number of solid precipitation, the solid material filter out, filter, with 2.9L dichloromethane solid solution Clear, magnetic stirrer slowly stirring.Weigh the s-p-methoxyphenylethylamine (151g), dissolved in 1.0L dichloromethane, the amine solution slowly added to the solution, dropping 40-50 minutes, the temperature control at 18 ~ 22 C, After the dropwise addition, the mixture was allowed to stand for 1 hour, and a large amount of fine granular solid and flocculent solid were precipitated. The granular solid sank into the bottom of the container and the floc floats on the upper part of the solution.After overnight, the supernatant was carefully poured out and the bottom solid was filtered and dried at 35 C under reduced pressure to give compound C, solid: 271 g.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(4-Methoxyphenyl)ethylamine, its application will become more common.

Reference:
Patent; Shanghai Jinhe Bio-pharmaceutical Co., Ltd.; Zhang Weizhong; Wang Quanyong; Cai Zhixia; Xie Bin; Feng Leiyu; Wu Yujuan; Tong Zebin; (12 pag.)CN106632368; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 6298-96-0, These common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, 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.

A suspension of tert-butyl 4-(2-(6-methoxypyridin-3-yl)-2-oxoethyl)piperidine-1 -carboxylate (3.00 g, 8.97 mmol) and (S)-1 -(4-methoxyphenyl)ethan-1 -amine (2.00 mL, 13.5 mmol) in titanium(IV) isopropoxide (7.89 mL, 26.9 mmol) was stirred at 90 C. The reaction progress was monitored by LCMS (aliquots treated with MeOH, NaBH4, followed by 1 N HCI). LCMS indicated complete reaction after 1 hour. The yellow solution was cooled to 0 C, diluted with MeOH (15 mL), treated slowly with NaBH4 (0.509 g, 13.46 mmol) in portions. After 1 hour, the solution was warmed to RT and stirred for an additional 4 hours.. The reaction was quenched with saturated aqueous NH4CI and 1 N HCI and then extracted with EtOAc. The EtOAc solution was washed with saturated aqueous NaHC03, brine, dried over Na2S04, filtered, and concentrated. 1H-NMR analysis of the crude material showed an approximately 2:1 mixture of SS : RS diastereomers. Purification by flash chromatography (silica gel, 0-100% EtOAc/hexanes, gradient elution) afforded tert- butyl 4-((S)-2-(((S)-1 -(4-methoxyphenyl)ethyl)amino)-2-(6-methoxypyridin-3- yl)ethyl)piperidine-1 -carboxylate (2.39 g, 57% yield) as clear oil. LCMS (ESI) m/z calcd for C27H39N3O4: 469.3. Found: 470.4 (M+1)+. NMR (400MHz, CDCI3) delta 7.85 (s, 1H), 7.48 (d, J = 8.6 Hz, 1H), 7.12 (d, J = 8.2 Hz, 2H), 6.87 (d, J = 8.2 Hz, 2H), 6.76 (d, J = 8.6 Hz, 1H), 4.08 – 3.88 (m, 5H), 3.82 (s, 3H), 3.40 (q, J = 6.4 Hz, 1H), 3.33 (t, J = 6.6 Hz, 1H), 2.67 – 2.43 (m, 2H), 1.66 – 1.48 (m, 2H), 1.47 – 1.16 (m, 15H), 1.09 – 0.82 (m, 2H).

Statistics shows that 1-(4-Methoxyphenyl)ethylamine is playing an increasingly important role. we look forward to future research findings about 6298-96-0.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; EVINDAR, Ghotas; KAZMIERSKI, Wieslaw Mieczyslaw; MILLER, John Franklin; SAMANO, Vicente; SUWANDI, Lita; TEMELKOFF, David; WASHIO, Yoshiaki; XIA, Bing; (152 pag.)WO2019/3142; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 6298-96-0 as follows. SDS of cas: 6298-96-0

To a 250 mL RBF was added (S)-1-(4-methoxyphenyl)ethanamine (6.39 g, 42.3 mmol), 1-(3- methylpyridin-2-yl)ethanone (6 g, 44.4 mmol), DCM (Volume: 106 ml) and STAB-H (17.92 g, 85 mmol) at rt and the reaction was stirred for 24h. The reaction was quenched by the addition of 1N NaOH until a pH of 8 was achieved. The phases were separated and the organic layer was treated with 1N NaOH until pH 11 was observed. The DCM layer was dried with MgSO4 filtered and concentrated to an oily residue. The residue was purified via combiflash to separate the diastereomers (~4:1 by crude NMR, 80g column 10-30% gradient over 40 min). 1H NMR (400 MHz, CDCl3): delta= 8.45 (d, J= 4.8 Hz, 1H), 7.34 (d, J= 7.6 Hz, 1H), 7.13 (d, J= 8.5 Hz, 2H), 7.04 (dd, J= 7.8, 4.6 Hz, 1H), 6.82 (d, J= 9.2 Hz, 2H), 3.79 (s, 3H), 3.74 (q, J= 6.0 Hz, 1H), 3.27 (q, J= 5.9 Hz, 1H), 1.24 (d, J= 6.3 Hz, 3H), 1.20 (d, J= 6.3 Hz, 3H); LC/MS 75% MeOH in H2O over 3 minutes, rt = 0.480 at 254 nM, MS (+) 271.2

According to the analysis of related databases, 6298-96-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EMORY UNIVERSITY; LIOTTA, Dennis C.; JECS, Edgars; WILSON, Robert James; NGUYEN, Huy Hoang; KIM, Michelle Bora; WILSON, Lawrence; MILLER, Eric James; TAHIROVIC, Yesim Altas; TRUAX, Valarie; KAISER, Thomas; (311 pag.)WO2018/156595; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem