Category: 41789-95-1

Reference of 41789-95-1,Some common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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.

General procedure: To a solution of 1,4-bis(bromomethyl)benzene (1 mmol) in anhydrous acetonitrile (10 mL) was added potassium carbonate (3 mmol) and the corresponding secondary amine (2.2 mmol). The reaction mixture was heated at reflux for 3 h. The resulting mixture was diluted with water (20 mL) and extracted with ethyl acetate (15 mL) three times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude was purified by column chromatography with methanol/dichloromethane (150:1, v/v) to give the title compound as a colorless liquid or a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(3-Methoxyphenyl)-N-methylmethanamine, its application will become more common.

Reference:
Article; Bai, Renren; Liang, Zhongxing; Yoon, Younghyoun; Liu, Shuangping; Gaines, Theresa; Oum, Yoonhyeun; Shi, Qi; Mooring, Suazette Reid; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 340 – 350;,
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Related Products of 41789-95-1, 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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In a 25 mL single neck flask, the intermediate 4 (0.4 g, 1.21 mmol), (3- methoxyphenyl)-N-methylmethanamine (1.09 g, 7.23 mmol), Cul (0.023 g, 0.12 mmol) and l-methylpyrrolidin-2-one (3 mL) were added and the resulting mixture was heated at 150 0 C for 12 h and worked up. The reaction mixture was partitioned in dichloromethane/water and the organic layer was separated. The organic phase was dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by prep-HPLC to obtain the pure 7-(N-(3-methoxybenzyl)-N-methylamino)-l-benzyl-6-fluoro-l, 4-dihydro-4- oxoquinoline – 3-carboxylic acid (25 mg); Yield: 4.63%; H NMR (400 MHz, CDCb): delta 15.0 (s, IH), 8.77 (s, IH), 8.01 (d, J=14, IH), 7.33 (s, 3H), 7.22-7.26 (t, IH), 7.04 (d, J=18.4, 2H), 6.82 (d, J=7.2, IH), 6.70-6.74 (m, 2H), 6.52 (d, J=5.6, IH), 5.30 (s, 2H), 4.43 (s, 2H), 3.71- 7.76 (m, 3H), 2.92(s, 3H); MS(ESI): 447.0(M+H); HPLC: 98.0%.

The synthetic route of 1-(3-Methoxyphenyl)-N-methylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIROGYONE THERAPEUTICS, INC.; SANDANAYAKA, Vincent; WU, Qiong; (80 pag.)WO2016/81464; (2016); 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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, A new synthetic method of this compound is introduced below., COA of Formula: C9H13NO

Step B: Ethyl acrylate (33.0 mL, 298 mmol) was added to a stirred mixture of benzylamine (15.0 g, 99.2 mmol) from Step A above and acetic acid (3 mL) at 0 C. The mixture was heated at 80 C. for 4 hours and allowed to cool to room temperature before diluting with dichloromethane (300 mL). The reaction mixture was washed with saturated NaHCO3, dried over Na2SO4 and concentrated in vacuo. The residue was treated with toluene and the resulting solution concentrated in vacuo in order to remove residual ethyl acrylate, affording the ester (25.0 g, 100%) as a colorless oil: 1H NMR (500 MHz, CDCl3) delta 7.22 (t, J=8.0 Hz, 1H), 6.89-6.86 (m, 2H), 6.78 (dd, J=8.2, 2.5 Hz, 1H), 4.13 (q, J=7.1 Hz, 2H), 3.80 (s, 3H), 3.48 (s, 2H), 2.74 (t, J=7.2 Hz, 2H), 2.51 (t, J=7.2 Hz, 2H), 2.21 (s, 3H), 1.25 (t, J=7.1 Hz, 3H).

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; AMR Technology, Inc.; US2007/21408; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 41789-95-1, These common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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.

General procedure: Amine (1.2 equiv) and 3-bromotoluene (1 equiv) were added to an aqueous solution of TPGS-750-M-2% (1 mL/mmol). The mixture was degassed by bubbling Argon in through (5 min). NaO-t-Bu (1.5 equiv), of [(allyl)PdCl]2 (1.1%) and cBridp (4.4%) were added together to the previous solution. The mixture was stirred (at 1200 rpm) at 50 C (2-24 h). Volatiles were evaporated and the crude residue was purified by chromatographic column on silica gel using ethyl acetate and cyclohexane as solvent.

Statistics shows that 1-(3-Methoxyphenyl)-N-methylmethanamine is playing an increasingly important role. we look forward to future research findings about 41789-95-1.

Reference:
Article; Salome, Christophe; Wagner, Patrick; Bollenbach, Maud; Bihel, Frederic; Bourguignon, Jean-Jacques; Schmitt, Martine; Tetrahedron; vol. 70; 21; (2014); p. 3413 – 3421;,
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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, A new synthetic method of this compound is introduced below., Safety of 1-(3-Methoxyphenyl)-N-methylmethanamine

General procedure: To a solution of bromobenzoyl chloride (2 mmol) was added the corresponding N-methylaniline (2 mmol) followed by Et3N (2 mmol) in CH2Cl2 (10 mL) at 0 C. After a few minutes, the ice bath was removed and the reaction mixture was warmed up to room temperature and stirred at room temperature overnight. The reaction mixture was extracted twice with CH2Cl2 (2 × 15 mL). The organic layer was dried over MgSO4, filtered and the solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography using hexanes and EtOAc as eluent or by trituration in a mixture of diethyl ether / petroleum ether to afford the desired compound.

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:
Article; Gargano, Emanuele M.; Allegretta, Giuseppe; Perspicace, Enrico; Carotti, Angelo; Van Koppen, Chris; Frotscher, Martin; Marchais-Oberwinkler, Sandrine; Hartmann, Rolf W.; PLoS ONE; vol. 10; 7; (2015);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 41789-95-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 41789-95-1 name is 1-(3-Methoxyphenyl)-N-methylmethanamine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

The title compound was prepared by reaction of 4-bromobenzoylchloride (329 mg, 1.5 mmol) and 3-methoxybenzylamine (227 mg, 1.5 mmol) in presence of triethylamine (0.24 ml, 1.73 mmol) according to method A. Purification by FC (n- hexane/ ethyl acetate 6 : 1) afforded the desired product (468 mg, 93%); MS (ESI) : 335 (M + H)+; *H N MR (CD3COCD3) : 2.80-2.92 (m, 3H), 3.80 (s, 3H), 4.52-4.69 (m, 2H), 6.79 (br s, 1 H), 6.86 (dd, J= 8.5, 2.2 Hz, 1 H), 6.95 (br s, 1 H), 7.28 (t, J= 7.9 Hz, 1 H), 7.44 (d, J= 7.9 Hz, 2H), 7.62 (br s, 2H); 13C NMR (CD3COCD3) : 55.3, 112.9, 113.6, 120.0, 123.1, 129.1, 129.4, 130.0, 131.7, 135.7, 139.1, 159.8.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(3-Methoxyphenyl)-N-methylmethanamine, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITAeT DES SAARLANDES; HARTMANN, Rolf; MARCHAIS-OBERWINKLER, Sandrine; XU, Kuiying; WERTH, Ruth; WO2012/117097; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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 41789-95-1, name: 1-(3-Methoxyphenyl)-N-methylmethanamine

Step B: A solution of 4-chlorocinnamic acid (2.0 g, 10.9 mmol) and N-methylmorpholine (1.7 mL, 15.3 mmol) in anhydrous methylene chloride (80 mL) was cooled to -20 C. and isobutyl chloroformate (1.5 mL, 11.6 mmol) was added dropwise. After 15 minutes, a solution of the amine from Step A above (1.66 g, 10.9 mmol) in anhydrous methylene chloride (20 mL) was added dropwise, then the reaction was allowed to warm to room temperature and stir under N2 for 3 hours. The mixture was washed with 1M sodium dihydrogen phosphate dihydrate (2×), H2O (2×), and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. Purification via flash column chromatography (1:1 ethyl acetate/hexanes) yielded the desired amide (2.82 g, 82%) as a white solid: 1H NMR (300 MHz, CDCl3) delta 7.70 (dd, J=15.3, 4.8 Hz, 1H), 7.48 (d, J=8.4 Hz, 1H), 7.39 (d, J=8.4 Hz, 1H), 7.35 (d, J=8.4 Hz, 1H), 7.30 (d, J=8.4 Hz, 1H), 7.40-7.26 (m, 1H), 6.91 (d, J=15.3 Hz, 1H), 6.83 (s, 1H), 6.83 (d, J=12.3 Hz, 1H), 6.77 (d, J=15.3 Hz, 1H), 4.67 (d, J=12.3 Hz, 2H), 3.80 (s, 3H), 3.08 (d, J=4.2 Hz, 3H); ESI MS m/z 316 [M+H]+.; Step B: A solution of 4-chlorocinnamic acid (2.0 g, 10.9 mmol) and N-methylmorpholine (1.7 mL, 15.3 mmol) in anhydrous methylene chloride (80 mL) was cooled to -20 C. Isobutyl chloroformate (1.5 mL, 11.6 mmol) was added dropwise. After 15 minutes, a solution of the product from Step A (1.66 g, 10.9 mmol) in anhydrous methylene chloride (20 mL) was added dropwise. The reaction was allowed to warm to room temperature and stir under N2 for 3 hours. The reaction mixture was then washed with 1 M NaH2PO4.2H2O (2×), H2O (2×), and brine, then dried over sodium sulfate, filtered, and concentrated in vacuo. Purification via flash column chromatography (1:1 ethyl acetate/hexanes) yielded the desired amide (2.82 g, 82%) as a white solid: 1H NMR (300 MHz, CDCl3) delta 7.70 (dd, J=15.3, 4.8 Hz, 1H), 7.48 (d, J=8.4 Hz, 1H), 7.39 (d, J=8.4 Hz, 1H), 7.35 (d, J=8.4 Hz, 1H), 7.30 (d, J=8.4 Hz, 1H), 7.29 (m, 1H), 6.91 (d, J=15.3 Hz, 1H), 6.83 (s, 1H), 6.80 (m, 1H), 6.77 (d, J=15.3 Hz, 1H), 4.69-4.65 (m, 2H), 3.80 (s, 3H), 3.09-3.07 (m, 3H); ESI MS m/z=316 [C18H18ClNO2+H]+.; Step B: A solution of 4-chlorocinnamic acid (2.0 g, 10.9 mmol) and N-methylmorpholine (1.7 mL, 15.3 mmol) in anhydrous methylene chloride (80 mL) was cooled to -20 C. and isobutyl chloroformate (1.5 mL, 11.6 mmol) was added dropwise. After 15 minutes, a solution of the amine from Step A above (1.66 g, 10.9 mmol) in anhydrous methylene chloride (20 mL) was added dropwise, then the reaction was allowed to warm to room temperature and stir under N2 for 3 hours. The mixture was washed with 1M sodium dihydrogen phosphate dihydrate (2×), H2O (2×), and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. Purification via flash column chromatography (1:1 ethyl acetate/hexanes) yielded the desired amide (2.82 g, 82%) as a white solid: 1H NMR (300 MHz, CDCl3) delta 7.70 (dd, J=15.3, 4.8 Hz, 1H), 7.48 (d, J=8.4 Hz, 1H), 7.39 (d, J=8.4 Hz, 1H), 7.35 (d, J=8.4 Hz, 1H), 7.30 (d, J=8.4 Hz, 1H), 7.40-7.26 (m, 1H), 6.91 (d, J=15.3 Hz, 1H), 6.83 (s, 1H), 6.83 (d, J=12.3 Hz, 1H), 6.77 (d, J=15.3 Hz, 1H), 4.67 (d, J=12.3 Hz, 2H), 3.80 (s, 3H), 3.08 (d, J=4.2 Hz, 3H); ESI MS m/z 316 [M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; AMR Technology, Inc.; US2007/21408; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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 41789-95-1, Application In Synthesis of 1-(3-Methoxyphenyl)-N-methylmethanamine

General procedure: At 0 C, a solution of 3(4)-bromobenzoyl chloride or 5-bromothiophene-2-carbonyl chloride (1 eq) in CH2Cl2 (2 ml/eq) was added drop wise to a solution of N-methylbenzylamine (1 eq) and triethylamine (1.15 eq) in CH2Cl2 (2 ml/eq). The mixture was kept stirred at 0 C for 3 h and evaporated under reduced pressure. The residue was purified by FC with n-hexane/ethyl acetate as eluant.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(3-Methoxyphenyl)-N-methylmethanamine, and friends who are interested can also refer to it.

Reference:
Article; Xu, Kuiying; Al-Soud, Yaseen A.; Wetzel, Marie; Hartmann, Rolf W.; Marchais-Oberwinkler, Sandrine; European Journal of Medicinal Chemistry; vol. 46; 12; (2011); p. 5978 – 5990;,
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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H13NO

Step C: To a solution of the acid (1.85 g, 7.6 mmol) from step B above and N-methyl morpholine (1.5 mL, 13.7 mmol) in dichloromethane (50 mL) at -20 C. was added isobutyl chloroformate (1.2 mL, 9.1 mmol) dropwise. The reaction solution was stirred at -20 C. for 45 minutes and then a solution of 3-(methoxybenzyl) methylamine (1.3 g, 8.4 mmol) in dichloromethane (10 mL) was added to it dropwise. The resultant solution was warmed to room temperature and stirred overnight. The reaction solution was then washed with water, saturated sodium bicarbonate and brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product obtained was purified by flash column chromatography (95:5 to 50:50 hexanes/ethyl acetate) to give the desired product (2.0 g, 78%) as a yellow oil: 1H NMR (CDCl3, 500 MHz) delta 7.96-7.86 (m, 3H), 7.59-7.37 (m, 2H), 7.34-7.26 (m, 2H), 7.04-6.78 (m, 4H), 4.70 (d, J=13.5 Hz, 2H), 3.80 (s, 3H), 3.10 (d, J=17.9 Hz, 3H).

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; AMR Technology, Inc.; US2007/21408; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 41789-95-1, 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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1 Preparation of (+/-)-8-methoxy-2-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine, fumarate salt Step A: To a mixture of (3-methoxybenzyl) methylamine (3.02 g, 20 mmol) and cesium carbonate (7.82 g, 24 mmol) in DMF (50 mL) was added cinnamyl bromide (4.47 g, 22 mmol). The reaction mixture was stirred at room temperature for 15 hours. The reaction mixture was diluted with water and extracted with 1:1 hexanes/ethyl acetate (3×). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated to provide the desired product (3.1 g, 58%): 1H NMR (CDCl3, 500 MHz) delta 7.39-7.37 (m, 2H), 7.32-7.29 (m, 2H), 7.23-7.20 (m, 2H), 6.93-6.91 (m, 2H), 6.81-6.78 (m, 1H), 6.54 (d, J=15.9 Hz, 1H), 6.31 (dt, J=15.9, 6.6 Hz, 1H), 3.81 (s, 3H), 3.52 (s, 2H), 3.19 (dd, J=6.6, 1.2 Hz, 2H), 2.25 (s, 3H); ESI MS m/z=268 [M+H]+. This crude product was used in the next step without further purification.; Example 2 Preparation of (+/-)-6-methoxy-2-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine, fumarate salt Step A: To a mixture of (3-methoxybenzyl)methylamine (3.02 g, 20 mmol) and cesium carbonate (7.82 g, 24 mmol) in DMF (50 mL) was added cinnamyl bromide (4.47 g, 22 mmol). The reaction mixture was stirred at room temperature for 15 hours. The reaction mixture was diluted with water and extracted with 1:1 hexanes/ethyl acetate (3×). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated to provide the desired product (3.1 g, 58%): 1H NMR (CDCl3, 500 MHz) delta 7.39-7.37 (m, 2H), 7.32-7.29 (m, 2H), 7.23-7.20 (m, 2H), 6.93-6.91 (m, 2H), 6.81-6.78 (m, 1H), 6.54 (d, J=15.9 Hz, 1H), 6.31 (dt, J=15.9, 6.6 Hz, 1H), 3.81 (s, 3H), 3.52 (s, 2H), 3.19 (dd, J=6.6, 1.2 Hz, 2H), 2.25 (s, 3H); ESI MS m/z=268 [M+H]+. This crude product was used in the next step 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-(3-Methoxyphenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMR Technology, Inc.; US2007/21408; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem