Category: 22483-09-6

22483-09-6, name is 2,2-Dimethoxyethanamine, 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. Safety of 2,2-Dimethoxyethanamine

Dimethoxybenzaldehyde (12.20 g, 73.42 mmol) was dissolved in benzene (200 mL) and aminoacetaldehyde dimethyl acetal (12.0 mL, 11.7 g, 111 mmol) was added. The mixture was stirred at reflux for 4 h using a Dean-Stark trap. The reaction mixture was then concentrated and dissolved in CHCI3 (250 mL). The solution was washed with water (4 x 150 mL) and brine (150 mL), dried (Na2S04) and concentrated, and the last traces of solvent were removed under vacuum to provide the imine (18.41 g, 99.1%) as a light yellow solid: mp 50-52 C. 1H NMR (300 MHz, CDC13) delta 8.18 (s, 1 H), 7.42 (s, 1 H), 7.15 (d, / = 8.4 Hz, 1 H), 6.86 (d, / = 8.4 Hz, 1 H), 4.65 (t, / = 5.1 Hz, 1 H), 3.92 (s, 3 H), 3.90 (s, 3 H), 3.74 (d, / = 5.1 Hz, 2 H), 3.40 (s, 6 H).

The synthetic route of 22483-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PURDUE RESEARCH FOUNDATION; CUSHMAN, Mark, S.; SONG, Yunlong; WO2011/94416; (2011); A1;,
Ether – Wikipedia,
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Application of 22483-09-6, A common heterocyclic compound, 22483-09-6, name is 2,2-Dimethoxyethanamine, molecular formula is C4H11NO2, 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: A solution of amino acetaldehyde dimethyl acetal 2a (10. 514 g, 1.081 mL, 10 mmol), purchased from Alfa Aesa, and an aldehyde (10 mmol) in dry ethanol was placed in a round bottom flask and stirred for 12 h. To that solution, sodium borohydride powder (0.567 g, 15 mmol) was added at 0 C slowly over 5 minutes. the solution was then warmed to room temperature. After stirring for 4 h, the reaction was quenched with 3 drops of water and the mixture was filtered through a pad of celite. The solvent was evaporated under reduced pressure, the residue was extracted with 100 mL of ethyl ether and washed with100 mL of water. The organic layer was dried over MgSO4 anhydrous. Ethyl ether was then evaporated and the resulted viscous liquid was purified by flash column chromatography (SiO2; 4:1 then 3:1 and finally 1:1hexanes/ethyl acetate).

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; Luu, Quang H.; Guerra, Jorge D.; Castaneda, Cecilio M.; Martinez, Manuel A.; Saunders, Jong; Garcia, Benjamin A.; Gonzales, Brenda V.; Aidunuthula, Anushritha R.; Mito, Shizue; Tetrahedron Letters; vol. 57; 21; (2016); p. 2253 – 2256;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 22483-09-6, 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 22483-09-6 as follows.

(3,4,5-Trimethoxybenzylidene)-(2,2-dimethoxyethyl)amine (11c). Aminoacetaldehyde dimethylacetal (20.0 mL, 19.5 g, 0.185 mol) was dissolved in chloroform (80 mL) and MgSO4 (15 g) was added. Then 3,4,5-trimethoxybenzaldehyde (10c, 10.03 g, 0.05112 mol) was also added and the mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with chloroform (70 mL), washed with water (4*150 mL), brine (150 mL), dried (Na2SO4), and concentrated to provide the pure imine as a colorless oil (14.47 g, 100%). 1H NMR (300 MHz CDCl3) 8.10 (s, 1H), 6.91 (s, 2H), 4.58 (t, J=5.4 Hz, 1H), 3.81 (s, 6H), 3.79 (s, 3H), 3.69 (s, J, =5.4 Hz, J2=1.2 Hz, 2H), 3.33 (s, 6H).

According to the analysis of related databases, 22483-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cushman, Mark S.; Ioanoviciu, Alexandra S.; Pommier, Yves G.; US2008/242692; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 22483-09-6, 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 22483-09-6 as follows.

A solution of phthalic anhydride (10.00 g), aminoacetaldehyde (7.81 g) and N,N-diisopropylethylamine (13.09 g) in toluene under an atmosphere of nitrogen was heated at 120 C for 16 h and then quenched with NH4C1(aq) (100 mL, 2 M). The aqueous phase was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered. The filtrate was concentrated to get the crude residue S-I-I (15.49 g, y: 98%).

According to the analysis of related databases, 22483-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NATIONAL HEALTH RESEARCH INSTITUTES; SHIH, Chuan; SHIA, Kak-Shan; WU, Chien-Huang; CHOI, Ming-Chen; SONG, Jen-Shin; WANG, Yun; (84 pag.)WO2018/132326; (2018); 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 22483-09-6 as follows. SDS of cas: 22483-09-6

50 g (270.2 mmol) 4-bromobenzaldehyde were dissolved in 200 ml of toluene and 28.4 g (270.2 mmol) aminoacetaldehyde dimethylacetal were added.. After the addition of 5.1 g (27.0 mmol) p-toluenesulfonic acid monohydrate, the reaction mixture was heated under reflux in a Dean Stark apparatus. After 4 h, the reaction was cooled to room temperature and washed with saturated sodium hydrogen carbonate-solution (2x) and water. The combined aqueous layers were extracted with Toluene and the combined organic layers were dried over magnesium sulfate and evaporated. The residue was dissolved in 200 ml of ethanol and 5.11 g (135.1 mmol) of sodium borohydride were added in small portions. After stirring for 2 h at room temperature and standing overnight, 5.0 ml acetic acid were added and the solvent was removed i. vac. The residue was taken up in dichloromethane and washed (2x) with water. After drying over magnesium sulfate and evaporation, 60.5 g of the title compound were obtained (crude product), which were used without further purification. Rt = 0.80 min (Method C). Detected mass: 274.1/276.1 (M+H+).

According to the analysis of related databases, 22483-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; WO2008/77552; (2008); 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. 22483-09-6, name is 2,2-Dimethoxyethanamine, A new synthetic method of this compound is introduced below., Quality Control of 2,2-Dimethoxyethanamine

General procedure: Benzaldehyde derivatives (1500 mg, 13.13 mmol) and Aminoacetaldehyde dimethyl acetal (19.70 mmol) were dissolved in 15 mL of methanol, NaBH(OAc)3 (19.70 mmol) was added at 0 C slowly in 3h. The reaction mixture was stirred at room temperature overnight and concentrated under reduced pressure. The residue was extracted with dicloromethane (DCM, 15 mL) three times, and the combined extracts were washed with 2N KOH, brine and dried over Na2SO4. The solution was filtered and added TEA (39.40 mmol) and TsCl (21.00 mmol) at 0C and stirred at room temperature for 5h. The resulting mixture was extracted with DCM (15 mL) three times. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (PE : EA = 5:1) to give the desired product.

The synthetic route of 22483-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shi, Zeyu; Xiao, Qiong; Yin, Dali; Chinese Chemical Letters; (2019);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 22483-09-6, These common heterocyclic compound, 22483-09-6, name is 2,2-Dimethoxyethanamine, 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-Bromo-benzyl)-(2,2-dimethoxy-ethyl)-amine (1); 50 g (270.2 mmol) 4-bromobenzaldehyde were dissolved in 200 ml toluene and 28.4 g (270.2 mmol) aminoacetaldehyde dimethylacetal were added. After the addition of 5.1 g (27.0 mmol) p-toluenesulfonic acid monohydrate, the reaction mixture was heated under reflux in a Dean Stark apparatus. After 4 h, the reaction was cooled to room temperature and washed with saturated NaHCO3-solution (2x) and H2O. The combined aqueous layers were extracted with toluene and the combined organic layers were dried with MgSO4 and evaporated. The residue was dissolved in 200 ml ethanol and 5.11 g (135.1 mmol) sodium borohydride were added in small portions. After stirring for 2 h at room temperature and standing overnight, 5.0 ml acetic acid were added and the solvent was removed i. vac. The residue was taken up in dichloromethane and washed (2x) with H2O. After drying with MgSO4 and evaporation, 60.5 g of the title compound were obtained (crude product), which were used without further purification. Rt = 0.80 min (Method C). Detected mass: 274.1/276.1 (M+H+).

Statistics shows that 2,2-Dimethoxyethanamine is playing an increasingly important role. we look forward to future research findings about 22483-09-6.

Reference:
Patent; SANOFI-AVENTIS; WO2008/77553; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem