Day: September 29, 2020

31886-58-5, 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. (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, cas is 31886-58-5,the chiral-nitrogen-ligands compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of (R)-Ugi?s amine 3 (2.57 g, 10 mmol) in TBME (20 mL) was added 1.6 M t-BuLi solution in n-hexane (6.8 mL, 10.88 mmol) at 0 C. After the addition was complete, the mixture was warmed to room temperature, and stirred for 1.5 h at room temperature. The mixture was then cooled to 0 C again, and Ar2PCl (11 mmol) was added in one portion. After stirring for 20 min at 0 C, the mixture was warmed to room temperature, and stirred for 1.5 h at room temperature. The mixture was then quenched by the addition of saturated NaHCO3 solution (20 mL). The organic layer was separated and dried over MgSO4, and the solvent was removed under reduced pressure, after which the filtrate was concentrated. The residue was purified by chromatography to afford 4a, 4e, and 4f.

The chemical industry reduces the impact on the environment during synthesis,31886-58-5,(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine,I believe this compound will play a more active role in future production and life.

Reference£º
Article; Nie, Huifang; Zhou, Gang; Wang, Quanjun; Chen, Weiping; Zhang, Shengyong; Tetrahedron Asymmetry; vol. 24; 24; (2013); p. 1567 – 1571;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Tris[2-(dimethylamino)ethyl]amine, A common heterocyclic compound, 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.”33527-91-2

To a solution of tris(2-dimethylaminoethyl)amine (0.426 g, 1.85mmol) in acetonitrile (4 mL) was added 1-bromodecane (1.27 g, 5.73 mmol). Theresulting mixture was heated at reflux with stirring for 18 hours. After cooling, and the addition of hexanes (5 mL), a white solid precipitated, which was filtered with a Buchner funnel, transferring with a cold hexanes/acetone mixture (15 mL, 1:1). The solid was rinsed with a cold hexanes/acetone mixture (2O mL, 1:1), resulting in T10 10,10,10 (1.16 g, 70%) as a white powder; mp=223-248 C; ?H NMR (300 MHz,CDC13) oe 4.11-4.02 (m, 6H), 3.62-3.53 (m, 6H), 3.41-3.27 (m, 24H), 1.72-1.62 (m, 6H), 1.38-1.14 (m, 42H), 0.85-0.78 (m, 9H); ?3C NMR (75 MHz, CD3OD) oe 65.4,61.1, 50.2, 46.9, 31.6, 29.2, 29.0, 28.9, 26.1, 22.4, 22.3, 13.0; high resolution mass spectrum (ESI) m/z 217.9095 ([Mj3 calculated for [C42H93N4j3: 217.9128). See alsoYoshimura et al., 2012, Langmuir 28:9322-9331. ?H and ?3C NMR spectra of compound T-10,10,10 can be found in Figure 50.

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 Tris[2-(dimethylamino)ethyl]amine, 33527-91-2

Reference£º
Patent; TEMPLE UNIVERSITY-OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; VILLANOVA UNIVERSITY; WUEST, William, M.; MINBIOLE, Kevin, P.C.; BARBAY, Deanna, L.; (227 pag.)WO2016/172436; (2016); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, A common heterocyclic compound, 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.”31886-58-5

a) Preparation of the chlorophosphine (X3)3.85 ml (5 mmol) of S-BuLi (1.3 M in cyclohexane) are added dropwise to a solution of 1.29 g (5 mmol) of (R)-1-dimethylamino-1-ferrocenylethane in 5 ml of TBME at <-20C. After stirring the mixture at the same temperature for 10 minutes, the temperature is allowed to rise to room temperature and the mixture is stirred for another 1.5 hours. The reaction mixture is then cooled to -78C and 0.62 ml (5 mmol) of dichloroisopropylphosphine is added dropwise at such a rate that the temperature does not exceed -60C. Further stirring at -78C for 30 minutes and subsequently at room temperature for one hour gives a suspension comprising the chlorophosphine X3; Example B17: Preparation of the compound (Rc,SFc,SP)-1-[2-(1-dimethylaminoethyl)ferrocen- i-yllcyclohexylphosphino-i '-bis-beta.S-d^trifluoromethylJphenyllphosphinoferrocene (B17):4 ml (10 mmol) of n-BuLi (2.5 M in hexane) are added dropwise to a solution of 3.44 g (10 mmol) of 1 ,1 '-dibromoferrocene in 10 ml of tetrahydrofuran (THF) at a temperature of < -30C. The mixture is stirred at this temperature for a further 1.5 hours to give a suspension of 1-bromo-1 '-lithioferrocene X5.In a second reaction vessel, 7.7 ml (10 mmol) of S-BuLi (1.3 M in cyclohexane) are added dropwise to a solution of 2.57 g (10 mmol) of (R)-1-dimethylamino-1-ferrocenylethane in 15 ml of TBME at <-10C. After stirring the mixture at the same temperature for 10 minutes, the temperature is allowed to rise to 0 and the mixture is stirred for another 1.5 hours. The reaction mixture is then cooled to -78C and 1.51 ml (10 mmol) of dichlorocyclohexyl- phosphine are added. Further stirring at -78C for 30 minutes and, after removal of cooling, at room temperature for another one hour gives a suspension of the chlorophosphine X4 which is subsequently added at a temperature of <-10C to the suspension of 1-bromo-1 '-lithio- ferrocene X5. The cooling is then removed and the mixture is stirred at room temperature for a further 1.5 hours. After renewed cooling to <-50C, 4 ml (10 mmol) of n-BuLi (2.5 M in hexane) are added dropwise. After the addition, the temperature is allowed to rise to 0C and the mixture is stirred for a further 30 minutes. It is then cooled to -20C and 4.63 g (10 mmol) of bis[3,5-di(trifluoromethyl)phenyl]chlorophosphine are added. The cooling is subsequently removed and the mixture is stirred at room temperature for another 1.5 hours. The reaction mixture is admixed with 1 N NaOH and extracted. The organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure on a rotary evaporator. The residue is subsequently heated at 150C for one hour. Chromatographic purification (silica gel 60; eluent = hexane/ethyl acetate 8:1 ) gives the compound B17 as a yellow solid (yield: 66%). 1H NMR (300 MHz, C6D6): delta 1.25 (d, 3H, J = 6.7 Hz), 1.00-2.29 (m, 1 1 H), 2.20 (s, 6H), 3.78 (m, 1 H), 4.02 (m, 1 H), 4.04 (s, 5H), 4.09 (m, 1 H), 4.14 (m, 1 H), 4.17 (m, 1 H), 4.21 (m, 1 H), 4.40 (m, 2H), 4.60 (m, 1 H), 7.80 (d, 2H, J = 6.8 Hz), 8.00 (d, 4H, J = 6.0 Hz). 31P NMR (121.5 MHz, C6D6): delta -27.1 (s); -14.1 (s).

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 (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, 31886-58-5

Reference£º
Patent; SOLVIAS AG; WO2007/116081; (2007); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

N1,N2-Dimethylethane-1,2-diamine, A common heterocyclic compound, 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.”110-70-3

Step 1 : To a solution of N,N’-dimethylethylenediamine (300 mg) in DMF (2.0 mL) was added K2C03 ( 1.0 g) and compound B (466 mg). The mixture was heated at 80C for 3h. Solvent was evaporated and the residue was extracted with DCM and then purified by a prep-TLC plate(10%MeOH/DCM with 1% NH3 in methanol) to give product as a yellow solid (400 mg, yield 75%).

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 N1,N2-Dimethylethane-1,2-diamine, 110-70-3

Reference£º
Patent; ARIAD PHARMACEUTICALS, INC.; DALGARNO, David, C.; HUANG, Wei-sheng; SHAKESPEARE, William, C.; WANG, Yihan; ZHU, Xiaotian; WO2012/151561; (2012); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Tris[2-(dimethylamino)ethyl]amine, A common heterocyclic compound, 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.”33527-91-2

To a solution of tris(2-dimethylaminoethyl)amine (0.326 g, 1.41 mmol) in acetonitrile (4 mL) was added 1-bromooctadecane (1.41g, 4.23 mmol). The resulting mixture was heated at reflux with stirring for 23 hours, during which time a white solid was observed. After cooling, and the addition of a cold hexanes/acetonemixture (15 mL, 1:1), to the reaction flask, the precipitate was filtered with a Buchner funnel, and rinsed with a cold hexanes/acetone mixture (20 mL, 1:1), resulting in T-18,18,18 (1.48 g, 85%) as a white powder; mp=227-259 C; ?H NMR (300 JVII-Tz, CDC13) oe 4.13-4.02 (m, 6H), 3.65-3.58 (m, 6H), 3.46-3.38 (m, 6H), 3.35 (s, 18H), 1.78-1.66 (m, 6H), 1.41-1.37 (m, 90H), 0.89-0.82 (m, 9H); high resolutionmass spectrum (ESI) in/z 330.0376 ([Mj3 calculated for [C66H,4,N4j3: 330.0380). ?H spectmm of compound T-18,18,18 can be found in Figure 55.

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 Tris[2-(dimethylamino)ethyl]amine, 33527-91-2

Reference£º
Patent; TEMPLE UNIVERSITY-OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; VILLANOVA UNIVERSITY; WUEST, William, M.; MINBIOLE, Kevin, P.C.; BARBAY, Deanna, L.; (227 pag.)WO2016/172436; (2016); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

N1,N2-Dimethylethane-1,2-diamine, A common heterocyclic compound, 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.”110-70-3

The ligand L1Q was synthesized via similar procedure mentionedabove [23]. To an aqueous solution of 2-(chloromethyl)-quinoline hydrochloride (2 g, 9.34 mmol), a solution of potassiumcarbonate (2.73 g, 18.66 mmol) in 10 mL water was added in dropwisemanner. The reaction mixture was stirred for 30 min at ambienttemperature. After stirring, the resulting solution wasextracted with dichloromethane (3 20 mL). The combinedorganic extracts were dried over anhydrous sodium sulfate andsolvent was evaporates under vacuum. The product 2-(chloromethyl)-quinoline was then dissolved in dichloromethane(10 mL) and was added dropwise to a solution of N,N0-dimethylethylenediamine (0.503 mL, 5.34 mmol) in 15 mL dichloromethane.After this addition, aqueous sodium hydroxide (10 mL,1 M) was added slowly. The reaction mixture was stirred for next60 h at room temperature, followed by rapid addition of anotherfraction of sodium hydroxide (10 mL, 10 mmol). The reaction mixturewas then extracted with dichloromethane (3 25 mL) andorganic portions were combined and dried over anhydrous sodiumsulfate. Volatile solvents were removed under vacuum to obtaincrude ligand L1Q as dark brown oil (1.68 g, Yield 85%). 1H NMR(500 MHz, Methanol-d4) d 7.57 (m, 2H, quinoline ring),7.63 (d,2H, quinoline ring), 7.73 (m, 2H, quinoline ring), 7.88 (d, 2H, quinolinering),7.98 (d, 2H, quinoline ring), 8.21 (d, 2H, quinoline ring),3.84 (s, 4H, -N-CH2-Quinoline), 2.71 (s, 4H, -CH2-CH2-), 2.32 (s,6H, -N-CH3). IR (cm1): 3384, 3056, 2946, 2800, 1617, 1598,1564, 1504, 1456, 1426, 1361, 1309, 1223, 1141, 1119, 1032,985, 951, 828, 784, 756, 619.

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 N1,N2-Dimethylethane-1,2-diamine, 110-70-3

Reference£º
Article; Singh, Nirupama; Niklas, Jens; Poluektov, Oleg; Van Heuvelen, Katherine M.; Mukherjee, Anusree; Inorganica Chimica Acta; vol. 455; (2017); p. 221 – 230;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Tris[2-(dimethylamino)ethyl]amine, A common heterocyclic compound, 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.”33527-91-2

General procedure: The copper complex Cu5-1 was dissolved in water, and an excessive amount of an aqueous solution of saturated sodium tetrafluoroborate (manufactured by Wako Pure Chemical Industries, Ltd.) was added while stirring. A precipitated solid was collected by filtering and a copper complex Cu5-72 was obtained.

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 Tris[2-(dimethylamino)ethyl]amine, 33527-91-2

Reference£º
Patent; FUJIFILM Corporation; Sasaki, Kouitsu; Kawashima, Takashi; Hitomi, Seiichi; Shiraishi, Yasuharu; US10215898; (2019); B2;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, A common heterocyclic compound, 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.”31886-58-5

4.0 ml (5.2 mmol) of S-BuLi (1.3 M in cyclohexanone) are added dropwise at -78C with stirring to a solution of 1.29 g (5 mmol) of compound 15 in 5 ml of TBME. The temperature is then allowed to rise to room temperature and the mixture is stirred further for 1.5 h. The resulting suspension is then injected with elevated pressure (argon) through a cannula into a second vessel in which a solution of 0.44 ml (5 mmol) of PCI3 in 10 ml of TBME is stirred at -78C. After the addition, the temperature is allowed to rise to 00C, and the resulting suspension is stirred further for another 1.5 hours. After adding 10 ml of THF, reaction solution 1 comprising compound 16 is obtained.

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 (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, 31886-58-5

Reference£º
Patent; Solvias AG; WO2007/135179; (2007); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

N1,N2-Dimethylethane-1,2-diamine, A common heterocyclic compound, 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.”110-70-3

Example 71Synthesis of tert-butyl methyl [2-(methylamino)ethyl]carbamate (VI-I) A solution of di-tert-butyl dicarbonate (2.18 g, 0.01 mol) in CH2Cl2 (120 mL) was added dropwise to a solution of N,N’-Dimethyl-ethane-1,2-diamine (1.76 g, 0.02 mol) in CH2Cl2 (40 mL) over 6 h with vigorous stirring. The reaction mixture was continued to stir for a further 18 h at room temperature. Then the solvent was concentrated in vacuo to give an oily residue, which was dissolved in 60 mL of 2M Na2CO3 aqueous solution, and extracted with CH2Cl2 (30 mL x 2). The combined organic layers were washed with 2M Na2CO3 (30 mL x 2), and dried over anhydrous MgSO4. The solvent was evaporated in vacuo to yield the product, which was purified by column chromatography (silica gel, CH2Cl2 : MeOH, 9: 1) to afford colorless oil (VI-I, 1.15 g, 61%)

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 N1,N2-Dimethylethane-1,2-diamine, 110-70-3

Reference£º
Patent; NORTHWESTERN UNIVERSITY; SILVERMAN, Richard, B.; JI, Haitao; LAWTON, Graham, R.; WO2008/42353; (2008); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, A common heterocyclic compound, 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.”31886-58-5

15.4 ml of a cyclohexane solution of s-butyllithium (1.3 M, 22 mmol) are added to a solution of 5.14 g (20 mmol) of (R)-N, N-dimethyl-1 -ferrocenylethylamine [(R)-ugi- amine] in 30 ml of t-butyl methyl ether (TBME) at <20C over a period of 10 minutes. The mixture is then heated to 00C while stirring and maintained at this temperature for 1.5 hours. It is then cooled to <60C and 3.0 ml (20 mmol) of dichlorocyclohexyl- phosphine are added over a period of 10 minutes. After stirring at -78C for30 minutes, the mixture is allowed to warm slowly to room temperature and is stirred at this temperature for 1.5 hours. 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 (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, 31886-58-5 Reference£º
Patent; SOLVIAS AG; WO2008/55942; (2008); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis