Category: 174799-52-1

Electric Literature of 174799-52-1, A common heterocyclic compound, 174799-52-1, name is tert-Butyl (2-(benzylamino)ethyl)carbamate, molecular formula is C14H22N2O2, 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.

41 c (5.00g, 17.96 mmol) and 56 (4.497g, 17.96 mmol, 1 eq) were dissolved in EtOH (30 mL) and a few drops of water added, before splitting the mixture into 2 x 30 mL W vessels. Each mixture was heated at 100 C for 30 mins in the MW reactor (dynamic program with maximum pressure 250 psi, maximum power 300W). Concentration of the reaction mixture gave approximately 10 g of crude residue. This was purified by FCC (eluent PE/DCM 1 :1 to prime/load the column, with the gradient increasing to 100% DCM over 5CV, 1 00% DCM for a further 3 CV and then raise to DCM/MeOH 99:1 over 1 CV, then to 95:5 over 3 CV, holding at this concentration to elute the desired product). This gave 7.30 (77%) g of white crystalline solid.

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; THE UNIVERSITY OF NOTTINGHAM; MISTRY, Shailesh; DARAS, Etienne; FROMONT, Christophe; JADHAV, Gopal; FISCHER, Peter Martin; KELLAM, Barrie; HILL, Stephen John; BAKER, Jillian Glenda; WO2012/4549; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 174799-52-1, name is tert-Butyl (2-(benzylamino)ethyl)carbamate, 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. Formula: C14H22N2O2

Tert-butyl(2-(benzylamino)ethyl)carbamate (Formula II, 50 g, 0.200 moles), 1,8-Diazabicycloundec-7-ene (61.12 ml, 0.401 moles) and DMF (300 ml) were charged in round bottom flask at RT and stirred to get heterogeneous solution. The reaction mixture was cooled to 0-5 C. and methyl vinyl ketone (75.3 ml, 0.903 moles) was added to the reaction mixture slowly over a period of 30 min. The resulting reaction mixture was stirred at room temperature for 16 h. After completion of the reaction, the reaction mixture was cooled to 0-5 C. and diluted with water (500 ml). The aqueous solution was extracted with ethyl acetate (250 ml*2). The organic layer was washed with 1N HCL (200 ml). The pH of aqueous layer was adjusted to 8 with saturated NaHCO3 solution (200 ml) and extracted with ethyl acetate (250 ml*2). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure at 45-50 C. to give tert-butyl(2-(benzyl(3-oxobutyl)amino)ethyl)carbamate (Formula III, 30 g, yield 46.87%) as a dark brown color liquid.

The synthetic route of tert-Butyl (2-(benzylamino)ethyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DR. REDDY’S LABORATORIES LIMTED; IQBAL, Javed; DAHANUKAR, Vilas Hareshwar; ORUGANTI, Srinivas; KANDAGATLA, Bhaskar; (23 pag.)US2016/168138; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 174799-52-1, name is tert-Butyl (2-(benzylamino)ethyl)carbamate, 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. name: tert-Butyl (2-(benzylamino)ethyl)carbamate

Preparation 64: Synthesis of tert-butyl 2-(N-benzyl-N-methylamino)ethylcarbamate (B)To a cooled (~5 C) solution of compound A (6.2 g, 25.0 mmol) and TEA (3.0 g, 29.7 mmol, 4.13 mL) in chloroform (50 mL) was added iodomethane (4.2 g, 29.7 mmol, 1.85 mL). The pressure tube was sealed, and the mixture stirred at ambient temperature for 20 h. The mixture was then precipitated with ether (300 mL); the white solid was filtered off and washed with ether (50 mL). The filtrate was concentrated and the residual yellow oil (5.2 g) was purified by silica gel column chromatography (2-10% MeOH gradient in DCM) to give compound B (3.3 g, 12.5 mmol, 50%) as a colorless oil. TLC Rf (DCM/MeOH 9:1): 0.55. LC-MS [M+H] 264.3 (C15H24N2O2 +H, calc: 264.4).

The synthetic route of tert-Butyl (2-(benzylamino)ethyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACOFORE, INC.; JENKINS, Thomas, E.; HUSFELD, Craig, O.; SEROOGY, Julie, D.; WRAY, Jonathan, W.; WO2011/133150; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 174799-52-1, name is tert-Butyl (2-(benzylamino)ethyl)carbamate, 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. Application In Synthesis of tert-Butyl (2-(benzylamino)ethyl)carbamate

Tert-butyl(2-(benzylamino)ethyl)carbamate (Formula II, 50 g, 0.200 moles), 1,8-Diazabicycloundec-7-ene (61.12 ml, 0.401 moles) and DMF (300 ml) were charged in round bottom flask at RT and stirred to get heterogeneous solution. The reaction mixture was cooled to 0-5 C. and methyl vinyl ketone (75.3 ml, 0.903 moles) was added to the reaction mixture slowly over a period of 30 min. The resulting reaction mixture was stirred at room temperature for 16 h. After completion of the reaction, the reaction mixture was cooled to 0-5 C. and diluted with water (500 ml). The aqueous solution was extracted with ethyl acetate (250 ml*2). The organic layer was washed with 1N HCL (200 ml). The pH of aqueous layer was adjusted to 8 with saturated NaHCO3 solution (200 ml) and extracted with ethyl acetate (250 ml*2). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure at 45-50 C. to give tert-butyl(2-(benzyl(3-oxobutyl)amino)ethyl)carbamate (Formula III, 30 g, yield 46.87%) as a dark brown color liquid.

The synthetic route of tert-Butyl (2-(benzylamino)ethyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DR. REDDY’S LABORATORIES LIMTED; IQBAL, Javed; DAHANUKAR, Vilas Hareshwar; ORUGANTI, Srinivas; KANDAGATLA, Bhaskar; (23 pag.)US2016/168138; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 174799-52-1, 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. 174799-52-1, name is tert-Butyl (2-(benzylamino)ethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of tert-butyl 2-(benzylamino)ethylcarbamate (2.8 g, 11.2 mmol) and 37% aqueous CH2O (1.0 mL, 11.2 mmol) in 1,2-dicholoroethane (35 mL) at RT was added NaHB(AcO)3 (3.7 g, 11.2 mmol). The mixture was stirred (RT, 16 h), diluted with saturated aqueous NaHCO3 (400 ml) and extracted with EA (3*300 ml). The organic layer was dried over MgSO4 and concentrated under reduced pressure to afford tert-butyl 2-(benzyl(methyl)amino)ethylcarbamate (1.38 g, 46.8%). 1H-NMR (CDCl3): delta7.25 (m, 5H, CH), 3.5 (s, 2H, CH2), 3.3 (m, 2H, CH2), 2.48 (m, 2H, CH2), 2.2 (s, 3H, CH3), 1.4 (s, 9H, CH3).

The synthetic route of tert-Butyl (2-(benzylamino)ethyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Milne, Jill C.; Jirousek, Michael R.; Bemis, Jean E.; Smith, Jesse J.; US2010/41748; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 174799-52-1, A common heterocyclic compound, 174799-52-1, name is tert-Butyl (2-(benzylamino)ethyl)carbamate, molecular formula is C14H22N2O2, 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.

41 c (5.00g, 17.96 mmol) and 56 (4.497g, 17.96 mmol, 1 eq) were dissolved in EtOH (30 mL) and a few drops of water added, before splitting the mixture into 2 x 30 mL W vessels. Each mixture was heated at 100 C for 30 mins in the MW reactor (dynamic program with maximum pressure 250 psi, maximum power 300W). Concentration of the reaction mixture gave approximately 10 g of crude residue. This was purified by FCC (eluent PE/DCM 1 :1 to prime/load the column, with the gradient increasing to 100% DCM over 5CV, 1 00% DCM for a further 3 CV and then raise to DCM/MeOH 99:1 over 1 CV, then to 95:5 over 3 CV, holding at this concentration to elute the desired product). This gave 7.30 (77%) g of white crystalline solid.

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; THE UNIVERSITY OF NOTTINGHAM; MISTRY, Shailesh; DARAS, Etienne; FROMONT, Christophe; JADHAV, Gopal; FISCHER, Peter Martin; KELLAM, Barrie; HILL, Stephen John; BAKER, Jillian Glenda; WO2012/4549; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 174799-52-1, name is tert-Butyl (2-(benzylamino)ethyl)carbamate, 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. category: amides-buliding-blocks

86.63 mg diphenyl cyanocarbonimidate, 52.1 mg isoquinolin-6-amine, and 6 ml THF were added to a reaction bottle with thermal reflux for 3.5 hrs. After removing THF by vacuum, the residue was added to 10 ml EA. The precipitated solid was filtered to obtain 32.9 mg 1-cyano-3-(isoquinolin-6-yl)-2-phenylisourea. The intermediate was reacted with equivalent tert-butyl-2-(benzylamino)ethylcarbamate and 20 mg of DIPEA in 5 ml DMF at 110 C. for 18 hrs. After cooling, 1N NaOH was added and extracted twice with EA. After the combined EA layer was dried and concentrated by Na2SO4, 26.4 mg intermediate product was eluted out by a SiO2 column (EA/Hexane 4:1). The intermediate was added to 1.5 ml 6N HCl at room temperature with stirring overnight. After the reaction solution was evaporated under reduced pressure, 2 ml acetone/methanol (10:1) was added. The precipitate was filtered and washed with acetone, and then the solid was taken and evaporated in vacuum to give 18.7 mg of product.

The synthetic route of tert-Butyl (2-(benzylamino)ethyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Industrial Technology Research Institute; CHEN, Chih-Hung; CHEN, Yi-Hsun; HUANG, Jui-Wen; HUANG, Kuo-Kuei; LIU, Chih-Peng; HWANG, Chrong-Shiong; (22 pag.)US2019/194137; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics