Category: 4584-46-7

These common heterocyclic compound, 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, 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. Recommanded Product: 2-Chloro-N,N-dimethylethanamine hydrochloride

NaN3(13.7 g, 210 mmol) was added into a solution of 2-chloro-N,N- dimethylethylamine hydrochloride (10.0 g, 70 mmol) in 100 mL water and the reaction mixture was heated to 70 C for overnight. The solution was basified with 4 M NaOH solution and extracted with anhydrous diethyl ether three times. The resulting solution was dried over MgS04 and concentrated to give volatile colorless oil. (5.9 g, 74%)1H NMR (CDC13, 400 MHz): delta 3.31 (t, 2H), 2.45 (t, 2H), 2.21 (s, 6H, N(CH3)2).

The synthetic route of 2-Chloro-N,N-dimethylethanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CORNELL UNIVERSITY; MA, Minglin; LIU, Qingsheng; (140 pag.)WO2018/140834; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 4584-46-7 as follows. HPLC of Formula: C4H11Cl2N

Provided in is step-by-step synthesis of PCA 1 and PCA 2. To make intermediate 3a 4-(2-(dimethylamino)ethoxy)-3-methoxybenzaldehyde, vanillin (1.52 g, 10 mmol), 2-chloro-dimethylethylamine HCI (2.16 g, 15 mmol), potassium iodide (332 mg, 2 mmol) and potassium carbonate (4.14 g, 30 mmol) were suspended in acetone and heated at reflux for 16 h. Next, volatiles were removed in vacuo and the resulting residue is redissolved in water and ethyl acetate. The organic layer was separated and washed with brine and dried with magnesium sulfate. Concentrating in vacuo resulted in 1.75 g (78%) of a yellow oil. NMR and mass spectrometry analysis of intermediate 3a 4-(2-(dimethylamino)ethoxy)-3-methoxybenzaldehyde is provided in to 4C: 1H NMR (400 MHz, Chloroform-d) delta9.82 (s, 1H), 7.41 (dd, J=8.2, 1.9 Hz, 1H), 7.37 (d, J=1.9 Hz, 1H), 6.96 (d, J=8.2 Hz, 1H), 4.17 (t, J=6.1 Hz, 2H), 3.89 (s, 3H), 2.79 (t, J=6.1 Hz, 2H), 2.32 (s, 6H). () 13C NMR (101 MHz, CDCl3) delta191.2, 154.0, 150.0, 130.3, 127.0, 111.7, 109.3, 67.4, 58.0, 56.2, 46.3. () ESI-MS [M+H]: Calculated: 224.1; Observed: 224.1 ()

According to the analysis of related databases, 4584-46-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Board of Trustees of the Leland Stanford Junior University; Velema, Willem Arend; Kool, Eric T.; (79 pag.)US2019/264205; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 4584-46-7, The chemical industry reduces the impact on the environment during synthesis 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, I believe this compound will play a more active role in future production and life.

A solution of 5-nitroindoline (6) (0.5 g, 3.05 mmol) in DMF (10 mL) was treated with NaH (0.39 g, 9.75 mmol, 60% wt in mineral oil) at 0 C resulting in an orange mixture. ;The reaction mixture was then treated with 2-chloro-N,N-dimethylethanamine hydrochloride (0.87 g, 6.09 mmol) resulting in a dark red mixture. ;The reaction was heated to 90 C and stirred for 1.5 h. ;After allowing the reaction to cool to room temperature, water was added and the product was extracted into EtOAc. ;The combined ethyl acetate layer was washed with water, brine and dried (Na2SO4). ;Solvent was evaporated and the crude was purified by flash column chromatography (2 M NH3 in MeOH:CH2Cl2, 2.5:97.5) to obtain the title compound (0.4 g, 56%) as a solid. 1H NMR (DMSO-d6) delta 7.96 (dd, 1H, J = 2.1, 8.7 Hz), 7.79 (d, 1H, J = 2.1 Hz), 6.49 (d, 1H, J = 9.0 Hz), 3.72 (t, 2H, J = 8.7 Hz), 3.39 (t, 2H, J = 6.6 Hz), 3.04 (t, 2H, J = 8.7 Hz), 2.44 (t, 2H, J = 6.3 Hz), 2.18 (s, 6H).

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-Chloro-N,N-dimethylethanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107,14;; ; Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 4584-46-7, 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. 4584-46-7 name is 2-Chloro-N,N-dimethylethanamine hydrochloride, 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.

To a round bottom flask with a stir-bar were added methyl 4-hydroxybenzoate (3.043 g, 20 mmol, 1.0 equiv.), 2-chloro-A,A-dimethylethylamine hydrochloride (3.457 g, 24 mmol, 1.2 equiv.), potassium carbonate (6.081 g, 44 mmol, 2.2 equiv.) and 30 mL isopropyl acetate. The mixture was heated at 75 C for 24 h, at which time all the methyl 4-hydroxybenzoate was consumed. Deionized water (30 mL) was then added to dissolve the potassium carbonate. The organic and aqueous phases were separated. The organic layer was washed with 30 mL water. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was evaporated and flash chromatography of the residue (gradient elution 5% methanol/EtOAc-lO% methanol/ EtOAc) gave the product, methyl 4-(2-(dimethylamino)ethoxy)benzoate (2.0 g, 45% yield), as a light yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-N,N-dimethylethanamine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; JUNG, Michael, E.; CHEN, Xiaohong; WANG, Cun-Yu; LI, Jiong; ZHENG, Jie; (167 pag.)WO2019/152536; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-Chloro-N,N-dimethylethanamine hydrochloride

To a mixture [OF 4-HYDROXYBENZALDEHYDE (1.] 34 g, 10.97 [MMOL)] and 2- dimethylaminoethyl chloride hydrochloride (1.95 g, 13.54 [MMOL)] in DMF (12 mL) was added KzCOs (6.04 g, 3.23 [MMOL).] The mixture was heated at reflux for 12 h. The residue was partitioned between [HZ0] and EtOAc. The organic layer was dried [(MGSO4),] filtered, and concentrated. The crude material was purified by flash chromatography [(10%] [MEOH/CH2CI2) TO YIELD 4-[2-(DIMETHYLAMINO) ETHOXYBENZALDEHYDE] (220 mg, 10%) as an orange liquid. ‘H NMR (400 MHz, CDCl3) 8 9. 87 (s, 1H), 7. [82 (D, 2H),] 7.01 (d, [2H),] 4.16 (t, [2H),] 2. [79 (T,] 2H), 2. 37 (s, 6H).

According to the analysis of related databases, 4584-46-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/9602; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 4584-46-7,Some common heterocyclic compound, 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, molecular formula is C4H11Cl2N, 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 mixture of 2-(2,4-dimethoxy-benzyl)-4-hydroxy-isoindole-1 ,3-dione (317 mg, 1.01 mmol), 2- dimethylaminoethyl chloride hydrochloride (160 mg, 1.11 mmol) and potassium carbonate (350 mg, 2.5 mmol) in DMF (4 mL) was heated at 6O0C for 18 hours. The mixture was concentrated in vacuo, taken up in ethyl acetate and extracted twice with 1 N hydrochloric acid. The aqueous extracts were made basic with solid potassium carbonate and extracted with ethyl acetate (*2). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to give the title compound (236 mg, 61%) as an off-white solid. 1H NMR (methanol-d4) 7.73 (1H, t), 7.44-7.40 (2H, m), 7.02 (1 H, d), 6.51 (1 H, d), 6.42 (1 H, dd), 4.72 (2H, s), 4.33 (2H, t), 3.80 (3H, s), 3.76 (3H, s), 2.87 (2H, t), 2.40 (6H, s). MS: [M+H]+ 385.

The synthetic route of 4584-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44029; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 4584-46-7, These common heterocyclic compound, 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, 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.

Intermediate 115yV,yV-Dimethyl-2-[4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazol-1 – yljethanamine4-(4,4,5,5-Tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 /-/-pyrazole (2 g, 10.31 mmol), cesium carbonate (6.72 g, 20.61 mmol) and 2-chloro-/V,/V-dimethylethanamine hydrochloride (2.227 g, 15.46 mmol) were suspended in acetonitrile (30 mL) and the mixture was heated at reflux for 5 h, then cooled to room temperature, diluted with Et20 and filtered. The filtrate was concentrated in vacuo to give N,N-dimethyl-2-[4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-1 H-pyrazol-1 -yl]ethanamine dimethyl{2-[4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-1 H-pyrazol-1 -yl]ethyl}amine (2.61 g, 9.84 mmol, 95 % yield) as an amber oil which was used in the next step without further purification.

Statistics shows that 2-Chloro-N,N-dimethylethanamine hydrochloride is playing an increasingly important role. we look forward to future research findings about 4584-46-7.

Reference:
Patent; GLAXOSMITHKLINE LLC; DEMONT, Emmanuel, Hubert; GARTON, Neil, Stuart; GOSMINI, Romain, Luc, Marie; HAYHOW, Thomas, George, Christopher; SEAL, Jonathan; WILSON, David, Matthew; WOODROW, Michael, David; WO2011/54841; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Chloro-N,N-dimethylethanamine hydrochloride

A mixture of the 4-hydroxybenzaldehyde (100g, 0.82mol) and anhydrous K2CO3 (330g,2.5mol) in EtOAc (1000mL) was stirring at 80 C till the disappearance of the startingmaterials 4-hydroxybenzaldehyde. Then 2-chloro-N, N-dimethylethanaminehydrochloride (118.69g, 0.83mol) was added into the reaction system and continued tostir until the reaction finished. After reaction, the mixture was filtered and the filtratewas washed with water and dried with Na2SO4. The extraction was filtered and thefiltrate was evaporated under reduced pressure to recycle the ethyl acetate and give thecrude mass which was further evaporated under high vacuum (bp142 -144oC/0.533 kPa)to give pale yellow oil(181.42g, 94%).

According to the analysis of related databases, 4584-46-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Feng, Chengliang; Yan, Bin; Yin, Guibo; Chen, Junqing; Ji, Min; Synlett; vol. 29; 17; (2018); p. 2257 – 2264;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Chloro-N,N-dimethylethanamine hydrochloride

Reference Example 6 Manufacture of 4-dimethylaminoethyloxy-benzenethiol Dimethylaminoethyl chloride hydrochloride (2.40 g; 17.1 mmol) and 5.83 g (42.2 mmol) of potassium carbonate were successively added to a solution (70 ml) of 3.00 g (13.6 mmol) of 4-iodophenol in N,N-dimethylformamide followed by stirring at 70C for 15 hours. The reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous saline solution, dried and concentrated. The resulting residue was purified by a silica gel column chromatography (chloroform: methanol = 30:1) to give 840 mg (yield: 21%) of an iodine derivative as an oily substance. _

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 4584-46-7.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1598349; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, belongs to chlorides-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 4584-46-7, Recommanded Product: 2-Chloro-N,N-dimethylethanamine hydrochloride

1) Production of N,N-dimethyl-2-(5-nitro-2,3-dihydro-1H-indol-1-yl)ethylamine: 730 mg of sodium hydride was added to an N,N-dimethylformamide solution of 1 g of 5-nitroindoline, and stirred at room temperature for 30 minutes. 1.8 g of 2-dimethylaminoethyl chloride hydrochloride was added to the reaction liquid, and stirred at 70C for 1 hour. The reaction liquid was cooled, diluted with chloroform, and washed with aqueous saturated sodium bicarbonate solution and saturated saline water in that order. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting crude product was purified through basic silica gel column chromatography (chloroform/methanol) to obtain 950 mg of the entitled compound as a yellow oil. 1H-NMR (CDCl3) delta: 8.26 (1H, dd, J=8.8, 2.4 Hz), 8.14 (1H, d, J=2.4 Hz), 6.96 (1H, d, J=8.8 Hz), 3.88 (2H, t, J=6.8 Hz), 3.64 (2H, s), 2.57 (2H, t, J=6.8 Hz), 2.30 (6H, s) ESI-MS Found: m/z [M+H] 250

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-N,N-dimethylethanamine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Banyu Pharmaceutical Co., Ltd.; EP2168966; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics