Category: 16793-91-2

Reference of 16793-91-2, 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. 16793-91-2, name is 2-Chlorophenethyl Bromide, This compound has unique chemical properties. The synthetic route is as follows.

Compound 28. 1 -(2-chlorophenethyl)-4-(2-methoxyphenethyl)piperidine A 250 mL round bottom flask was equipped with a magnetic stir bar, and then charged with 5 grams (0.0537 mol) of 4-picoline, 8.77 grams (0.0644 mol) of 2- methoxybenzaldehyde, and 50 ml of acetic anhydride. The reaction mass was heated to reflux and maintained at that temperature for 72 hours. The reaction mixture was then cooled to room temperature, and subjected to silica chromatography. Yield of (E)-4-(2- methoxystyryl)pyridine was 7.15 grams (63%). The 7.15 grams of (E)-4-(2- methoxystyryl)pyridine was then charged into a 500 mL hydrogenation flask, to which was added 100 mL of acetic acid as well as 50 mg of Pt02. The reaction mass was subjected to 45 psi of hydrogen gas, and allowed to react at room temperature for 16 hours. The reaction mixture was then filtered through a pad of celite, evaporated, basified with aqueous Na2C03 solution, and extracted with dichloromethane. The combined extraction solvents were removed under reduced pressure via rotovap. The residue was then subjected to silica chromatography, yielding 6.1 grams (82.1 % yield) of 4-(2-methoxyphenethyl)piperidine. A 100 mL round bottom flask equipped with a magnetic stir bar was then charged with 1.0 grams of 4-(2-methoxyphenethyl)piperidine (0.0046 mol), 1 .41 grams of 2- chlorophenethyllbromide (0.0064 mol), 1.87 grams of K2C03 (0.0135 mol), and 20 mL of DMF as solvent. The reaction mass was then heated to 70 C for 24 hours. The excess DMF was removed via reduced pressure, partitioned with water and dichloromethane, the organic layer separated; excess solvent removed under reduced pressure and the residue was subjected to silica chromatography. Yield of l-(2-chlorophenethyl)-4-(2- methoxyphenethyl)piperidine was 1.12 grams (68.0% yield). 1H NMR (300 MHz, CDC13) delta 1.40-1.62 (m, 7H), 2.41-2.75 (m, 10H), 3.84 (s, 3H), 6.92-7.73 (m, 8H) ppm.

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

Reference:
Patent; UNIVERSITY OF KENTUCKY RESEARCH FOUNDATION; CROOKS, Peter, A.; DWOSKIN, Linda, P.; CULVER, John; NICKELL, Justin, R.; ZHENG, Guangrong; WO2014/144064; (2014); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 16793-91-2,Some common heterocyclic compound, 16793-91-2, name is 2-Chlorophenethyl Bromide, molecular formula is C8H8BrCl, 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.

Example 14: Preparation of 8-[2-(2-chlorophenyl)ethyl]-3-methyl-4-({4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl)-1-oxa-8-azaspiro[4.5]dec-3-en-2-one [Show Image] A mixture of 3-methyl-4-({4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl)-1-oxa-8-azaspiro[4.5]dec-3-en-2-one dihydrochloride (Example 1 , 200 mg, 0.40 mmol), anhydrous potassium carbonate (180 mg, 1.30 mmol) and 1-(2-bromo-ethyl)-2-chlorobenzene (0.07 mL, 0.22 mmol) in anhydrous N,N-dimethylformamide (3 mL) was heated at 90C for 1.5 hours under microwave irradiation. The reaction mixture was concentrated under vacuum. The residue was taken up in dichloromethane (20 mL), washed with water (20 mL) and brine (20 mL), dried (MgSO4) and concentrated under vacuum. After purification by flash chromatography (silica), the title compound was obtained as a white solid (76 mg, 34%). 1H NMR (DMSO-d6, 400 MHz): delta 7.46-7.34 (m, 3H), 7.26-7.23 (m, 4H), 7.11 (d, J = 7.5 Hz, 1 H), 3.80-3.79 (m, 1H), 3.68-3.69 (m, 1H), 3.56 (s, 2H), 3.27 (s, 1H), 3.16-3.15 (m, 2H), 2.93-2.92 (m, 1H), 2.87-2.83 (m, 4H), 2.53 (s, 2H), 2.25-2.24 (m, 3H), 1.88-1.87 (m, 1H), 1.76 (s, 3H), 1.72 (s, 1H), 1.52 (s, 1H). LCMS (Method D): Mass found (M+ 562), Rt (min): 4.64, Area (%): 99.5 (Max), 99.6 (254 nm). HPLC (Method A): Rt (min): 4.61, Area (%): 98.5 (Max), 99.3 (254 nm).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chlorophenethyl Bromide, its application will become more common.

Reference:
Patent; Ares Trading SA; EP2508526; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 16793-91-2, 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 16793-91-2 as follows.

General procedure: General synthetic procedure for the final products.The appropriately substituted 4-phenethylpiperidine (6)(0.5 mmol) was dissolved in acetonitrile (5 mL) and K2CO3(0.75 mmol) and the appropriate phenethyl bromide (7) (0.5 mmol) added. The reaction mixture was refluxedfor 8 h.After completion of the reaction (monitored by TLC), the reaction mixture was cooled to ambient temperature and filtered through a Celite pad. The filtrate was concentrated under vacuum to obtain the desired crude product. The crude product was further purified by column chromatography (silica gel: 3-5% methanol in dichloromethane) to afford the corresponding 1,4-diphenethylpiperidine (8a-8y) in good yield (75-80 %), which was then converted to hydrochloride salt by treatment with 2M HCl in diethyl ether.Compounds12a-12dwere synthesized using the same procedure as above, except that an appropriately substituted 4-benzylpiperidine (11) was utilized in place of compound6.

According to the analysis of related databases, 16793-91-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nickell, Justin R.; Culver, John P.; Janganati, Venumadhav; Zheng, Guangrong; Dwoskin, Linda P.; Crooks, Peter A.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 13; (2016); p. 2997 – 3000;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 16793-91-2, 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. 16793-91-2, name is 2-Chlorophenethyl Bromide, This compound has unique chemical properties. The synthetic route is as follows.

Example 58 Preparation of 6-(2-chlorophenethyl)-1.2.3.4.5.6-hexahvdro-3.9- dimethylazepmor4.5-b1mdole (Compound No 69)[0423] The title compound was prepared by following general procedure 4 3,9-Dimethyl- l,2,3,4,5,6-hexahydroazepmo[4,5-b]mdole (214 mg, 1 0 mmol) was taken with copper iodide(19 mg, 0 1 mmol), L-pralme (23 mg, 0 2 mmol), potassium phosphate t?basic (426 mg, 2 0 mmol), l-(2-bromoethyl)-2-chlorobenzene (219 mg, 1 0 mmol) and DMF was added, the reaction was stirred at 900C under argon atmosphere for 12 h and monitored by LCMS After completion of the reaction water was added and extracted with ethyl acetate The organic layer was washed with water, dried over sodium sulfate and concentrated under vacuum The crude product was purified by reverse phase chromatography to afford 50 mg of the title compound (10 7%)

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

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; HUNG, David, T.; PROTTER, Andrew, Asher; JAIN, Rajendra, Parasmal; CHAKRAVARTY, Sarvajit; GIORGETTI, Marco; WO2010/51503; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 16793-91-2, These common heterocyclic compound, 16793-91-2, name is 2-Chlorophenethyl Bromide, 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: General synthetic procedure for the final products.The appropriately substituted 4-phenethylpiperidine (6)(0.5 mmol) was dissolved in acetonitrile (5 mL) and K2CO3(0.75 mmol) and the appropriate phenethyl bromide (7) (0.5 mmol) added. The reaction mixture was refluxedfor 8 h.After completion of the reaction (monitored by TLC), the reaction mixture was cooled to ambient temperature and filtered through a Celite pad. The filtrate was concentrated under vacuum to obtain the desired crude product. The crude product was further purified by column chromatography (silica gel: 3-5% methanol in dichloromethane) to afford the corresponding 1,4-diphenethylpiperidine (8a-8y) in good yield (75-80 %), which was then converted to hydrochloride salt by treatment with 2M HCl in diethyl ether.Compounds12a-12dwere synthesized using the same procedure as above, except that an appropriately substituted 4-benzylpiperidine (11) was utilized in place of compound6.

Statistics shows that 2-Chlorophenethyl Bromide is playing an increasingly important role. we look forward to future research findings about 16793-91-2.

Reference:
Article; Nickell, Justin R.; Culver, John P.; Janganati, Venumadhav; Zheng, Guangrong; Dwoskin, Linda P.; Crooks, Peter A.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 13; (2016); p. 2997 – 3000;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 16793-91-2, 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. 16793-91-2, name is 2-Chlorophenethyl Bromide, This compound has unique chemical properties. The synthetic route is as follows.

Compound 28. 1 -(2-chlorophenethyl)-4-(2-methoxyphenethyl)piperidine A 250 mL round bottom flask was equipped with a magnetic stir bar, and then charged with 5 grams (0.0537 mol) of 4-picoline, 8.77 grams (0.0644 mol) of 2- methoxybenzaldehyde, and 50 ml of acetic anhydride. The reaction mass was heated to reflux and maintained at that temperature for 72 hours. The reaction mixture was then cooled to room temperature, and subjected to silica chromatography. Yield of (E)-4-(2- methoxystyryl)pyridine was 7.15 grams (63%). The 7.15 grams of (E)-4-(2- methoxystyryl)pyridine was then charged into a 500 mL hydrogenation flask, to which was added 100 mL of acetic acid as well as 50 mg of Pt02. The reaction mass was subjected to 45 psi of hydrogen gas, and allowed to react at room temperature for 16 hours. The reaction mixture was then filtered through a pad of celite, evaporated, basified with aqueous Na2C03 solution, and extracted with dichloromethane. The combined extraction solvents were removed under reduced pressure via rotovap. The residue was then subjected to silica chromatography, yielding 6.1 grams (82.1 % yield) of 4-(2-methoxyphenethyl)piperidine. A 100 mL round bottom flask equipped with a magnetic stir bar was then charged with 1.0 grams of 4-(2-methoxyphenethyl)piperidine (0.0046 mol), 1 .41 grams of 2- chlorophenethyllbromide (0.0064 mol), 1.87 grams of K2C03 (0.0135 mol), and 20 mL of DMF as solvent. The reaction mass was then heated to 70 C for 24 hours. The excess DMF was removed via reduced pressure, partitioned with water and dichloromethane, the organic layer separated; excess solvent removed under reduced pressure and the residue was subjected to silica chromatography. Yield of l-(2-chlorophenethyl)-4-(2- methoxyphenethyl)piperidine was 1.12 grams (68.0% yield). 1H NMR (300 MHz, CDC13) delta 1.40-1.62 (m, 7H), 2.41-2.75 (m, 10H), 3.84 (s, 3H), 6.92-7.73 (m, 8H) ppm.

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

Reference:
Patent; UNIVERSITY OF KENTUCKY RESEARCH FOUNDATION; CROOKS, Peter, A.; DWOSKIN, Linda, P.; CULVER, John; NICKELL, Justin, R.; ZHENG, Guangrong; WO2014/144064; (2014); A2;,
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. 16793-91-2, name is 2-Chlorophenethyl Bromide, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Chlorophenethyl Bromide

Example 14: Preparation of 8-r2-(2-chlorophenyl)ethvn-3-methyl-4-((4-r3- (trifluoromethyl)phenynpiperazin-1-yl>carbonyl)-1-oxa-8-azaspiror4.51dec-3-en-2-oneA mixture of 3-methyl-4-({4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl)-1 -oxa-8- azaspiro[4.5]dec-3-en-2-one dihydrochloride (Example 1 , 200 mg, 0.40 mmol), anhydrous potassium carbonate (180 mg, 1.30 mmol) and 1-(2-bromo-ethyl)-2-chloro-benzene (0.07 mL, 0.22 mmol) in anhydrous N.N-dimethylformamide (3 mL) was heated at 90C for 1.5 hours under microwave irradiation. The reaction mixture was concentrated under vacuum. The residue was taken up in dichloromethane (20 mL), washed with water (20 mL) and brine (20 mL), dried (MgS0 ) and concentrated under vacuum. After purification by flash chromatography (silica), the title compound was obtained as a white solid. 1H NMR (DMSO-d6, 400 MHz): delta 7.46-7.34 (m, 3H), 7.26-7.23 (m, 4H), 7.11 (d, J = 7.5 Hz, 1 H), 3.80-3.79 (m, 1 H), 3.68-3.69 (m, 1 H), 3.56 (s, 2H), 3.27 (s, 1 H), 3.16-3.15 (m, 2H), 2.93-2.92 (m, 1 H), 2.87-2.83 (m, 4H), 2.53 (s, 2H), 2.25-2.24 (m, 3H), 1.88-1.87 (m, 1 H), 1.76 (s, 3H), 1.72 (s, 1 H), 1.52 (s, 1 H). LCMS (Method D): Mass found (M+ 562), Rt (min): 4.64, Area (%): 99.5 (Max), 99.6 (254 nm). HPLC (Method A): Rt (min): 4.61 , Area (%): 98.5 (Max), 99.3 (254 nm).

According to the analysis of related databases, 16793-91-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARES TRADING S.A.; JORAND-LEBRUN, Catherine; SWINNEN, Dominique; GERBER, Patrick; KULKARNI, Santosh; WO2012/130915; (2012); 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 16793-91-2 as follows. Product Details of 16793-91-2

Example 8A Di-tert-butyl (2-{5-[2-(2-chlorophenyl)ethoxy]-1-benzofur-2-yl}-2-oxoethyl)[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]malonate To a mixture of 100 mg (0.18 mmol) of the compound from Example 7A in 2.5 ml of acetonitrile were added 47 mg (0.21 mmol) of 1-(2-bromoethyl)-2-chlorobenzene and 49 mg (0.36 mmol) of potassium carbonate and the mixture was stirred under reflux for 1.5 h. Then, a further 47 mg (0.21 mmol) of 1-(2-bromoethyl)-2-chlorobenzene and 49 mg (0.36 mmol) of potassium carbonate were added and the mixture was stirred under reflux for a further 4.5 h. Then, the mixture was left to stand firstly overnight at RT and then, after another addition of 47 mg (0.21 mmol) of 1-(2-bromoethyl)-2-chlorobenzene, stirred for a further 5 h at 50 C. After cooling to RT, the mixture was admixed with 1 ml of water and purified directly by preparative HPLC (Method 7). The combined product-containing fractions were neutralized with saturated aqueous sodium hydrogencarbonate solution, concentrated to a residual volume of aqueous phase and extracted twice with dichloromethane. The combined organic phases were dried over magnesium sulphate and concentrated, and the residue was dried in vacuo. 21 mg (17% of theory, purity 100%) of the title compound were obtained. LC/MS (Method 1, ESIpos): Rt=1.59 min, m/z=702 [M+H]+.

According to the analysis of related databases, 16793-91-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BECK, Hartmut; LI, Volkhart Min-Jian; CANCHO GRANDE, Yolanda; TIMMERMAN, Andreas; BROHM, Dirk; JOeRIssEN, Hannah; BOGNER, Pamela; GERISCH, Michael; LANG, Dieter; (120 pag.)US2017/121315; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 16793-91-2, 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. 16793-91-2 name is 2-Chlorophenethyl Bromide, 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.

General procedure: Ethyl 2-piperidin-4-ylacetate 11 (1 g, 5.84 mmol, 1.0 equiv.) and substituted (2-romoethyl)benzene derivatives (12a-b) (7.01 mmol, 1.2 equiv.) were dissolved in 20 mL acetone.Then, anhydrous K2CO3 (11.68 mmol, 2 equiv.) and catalytic amount KI were added. The reactionmixture was refluxed for 4 h. After completion of the reaction, acetone was concentrated, and theresidue was dissolved in water (60 mL) and extracted with ethyl acetate (60 ¡Á 3 mL). The combinedorganic layers were dried over Na2SO4, filtered, and concentrated in vacuum. The obtained oil wasused in further synthesis without purification yielded compounds 13a-b (Yields were 67% and 72%).Then, 4 mol/L KOH (2.5 equiv.) was added to the solution of compounds 13a-b in C2H5OH: H2O =5:1(6 mL). The reaction mixture was stirred at room temperature for 7 h. After completion of the reaction, the reaction mixture was evaporated to dryness after neutralization with dilute hydrochloricacid solution. Poured into ethyl acetate to deposit the solid, after cooling off, the mixture was filteredand washed with cold ethyl acetate to give compounds 14a-d.Finally, intermediates (14a-b) (1.2 equiv.), PyBOP (1.2 equiv.) and DIPEA (1.5 equiv.) wereadded to 6 mL DMF and stirred at room temperature for 20 min. Then, intermediates (15a-b) (1.0equiv.) was added and stirred at room temperature for 4 h. After completion of the reaction, thereaction mixture was quenched with saturated NaCl solution. The aqueous phase was extracted withDCM. The DCM layer was combined and washed with brine solution. The organic layer was driedover anhydrous Na2SO4 and the solvent was removed under reduced pressure. After concentration,the crude product was purified by silica gel column chromatograph using a methanol indichloromethane gradient (DCM:methanol = 60:1-5:1) yielded compounds 16a-d.N-(1H-Indol-5-yl)-2-(1-phenethylpiperidin-4-yl)acetamide (16a). 2-(1-Phenethylpiperidin-4-yl) aceticacid (140 mg, 0.57 mmol), 1H-Indol-5-amine (63 mg, 0.48 mmol), PyBOP (295 mg, 0.57 mmol),DIPEA (93 mg, 0.72 mmol), DMF (6 mL). Yellow solid, m.p.: 165-167 C, yield: 80.70%, 1H NMR(400 MHz, CD3OD) delta 7.74 (d, J = 2.0 Hz, 1H), 7.28 (tt, J = 13.1, 6.8 Hz, 6H), 7.20 (d, J = 3.1 Hz, 1H),7.15 (dd, J = 8.6, 2.0 Hz, 1H), 6.37 (d, J = 3.1 Hz, 1H), 3.60 (d, J = 14.9 Hz, 2H), 3.26 (d, J = 5.0 Hz, 1H),3.08-3.01 (m, 3H), 2.39 (d, J = 7.0 Hz, 2H), 2.21-2.13 (m, 1H), 2.04 (d, J = 15.4 Hz, 2H), 1.74-1.60 (m,2H), 1.27 (s, 2H). 13C NMR (151 MHz, CD3OD) delta 170.66, 136.38, 133.81, 129.79, 128.59, 128.42, 127.97,126.86, 125.29, 115.83, 115.76, 112.47, 110.75, 101.07, 72.24, 70.09, 60.80, 57.69, 53.42, 52.37, 41.90,31.68, 31.23, 29.38, 28.89, 22.34, 13.05. HRMS (ESI): calcd. For C23H27N3O [M + H]+ 362.2227, found362.2242.

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

Reference:
Article; Guo, Yan; Yang, Hongyu; Huang, Zhongwei; Tian, Sen; Li, Qihang; Du, Chenxi; Chen, Tingkai; Liu, Yang; Sun, Haopeng; Liu, Zongliang; Molecules; vol. 25; 3; (2020);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

16793-91-2, name is 2-Chlorophenethyl Bromide, belongs to chlorides-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. category: chlorides-buliding-blocks

Example 51 Preparation of 6-(2-chlorophenethyl)-9-chloro-1.2.3.4.5.6-hexahvdro-3- methylazepmor4.5-b1mdole (Compound No 29)[0416] The title compound was prepared by following general procedure 4 9-Chloro-6-(2- chlorophenethyl)-3-methyl-l,2,3,4,5,6-hexahydroazepmo[4,5-b]mdole 9-chloro-3-methyl- l,2,3,4,5,6-hexahydroazepmo[4,5-b]mdole (0 234 g,l mmol) along with tetrabutylammomum chloride (0 026 g, 0 094 mmol) were taken into 50% aq NaOH solution (4 mL) and stirred for 15 mm at RT, l-(2-bromoethyl)-2-chlorobenzene (0 878 g, 4 mmol) was added and stirred for 10 mm at RT and then the reaction mixture was heated at 100 0C for overnight Product detected by LCMS The product was extracted in ethyl acetate, dried over anhydrous sodium sulfate, concentrated and purified by reverse phase chromatography to get pure compound 9- chloro-6-(2-chlorophenethyl)-3-methyl-l,2,3,4,5,6-hexahydro azepmo[4,5-b]mdole as the TFA salt (70 mg)

The synthetic route of 16793-91-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; HUNG, David, T.; PROTTER, Andrew, Asher; JAIN, Rajendra, Parasmal; CHAKRAVARTY, Sarvajit; GIORGETTI, Marco; WO2010/51503; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics