Day: August 28, 2020

As a common heterocyclic compound, it belong chiral-nitrogen-ligands compound,N1,N2-Dimethylethane-1,2-diamine,110-70-3,Molecular formula: C4H12N2,mainly used in chemical industry, its synthesis route is as follows.,110-70-3

The ligand 345BPMEN was synthesized by modifying thepreviously reported procedure (Singh et al. 2017). To a solutionof 2-chloromethyl-4-methoxy-3,5-dimethylpyridinehydrochloride 2.032 g (9.15 mmol) in 10 mL of water, asolution of potassium carbonate (2.55 g, (18.45 mmol) inwater (10 mL) was added dropwise. After potassium carbonateaddition, very thick white ppts were formed and solutionsolidified. Additional amount of water (50 mL) was addedinto the mixture. After water addition, the reaction mixturewas stirred at room temperature for next 30 min followed bysolvent extraction with dichloromethane (3 ¡Á 20 mL). Thecombined dichloromethane layer was treated with anhydroussodium sulfate. The solution was filtered, and the solventwas removed by rotatory evaporation. The collected light brown oil was dissolved in dichloromethane (10 mL).The above solution was added dropwise to a solution ofN,N?-dimethylethylenediamine 0.493 mL (4.58 mmol) indichloromethane (15 mL). Aqueous solution of 1 M sodiumhydroxide (10 mL) was slowly added and solution wasstirred for additional 60 h at room temperature. After 60 hof stirring was the rapid addition of a second fraction ofaqueous 1 M sodium hydroxide (10 mL, 10 mmol), the productwas extracted with dichloromethane (3 ¡Á 25 mL). Thecombined organic layers were dried over anhydrous sodiumsulfate and filtered. Subsequently, the excess solvent wasevaporated by vacuum to afford brown color viscous oil(1.71 g, Yield 97%). 1H NMR (500 MHz, Methanol-d4) delta8.08 (s, 2H, pyridine ring), 3.76 (s, 6H, -O-CH3-Py), 3.57(s, 4H, -CH2-CH2-Py), 2.56 (s, 4H, -CH2-CH2-), 2.28 (d,6H, CH3-Py), 2.24 (d, 6H, CH3-Py), 2.16 (s, 6H, -N-CH3).ESI-MS+: [345BPMEN + H]+ = 387.32 m/z+ (experimental)387.27 m/z+ (theoretical).

With the synthetic route has been constantly updated, we look forward to future research findings about N1,N2-Dimethylethane-1,2-diamine,belong chiral-nitrogen-ligands compound

Reference£º
Article; Botcha, Niharika Krishna; Gutha, Rithvik R.; Sadeghi, Seyed M.; Mukherjee, Anusree; Photosynthesis Research; vol. 143; 2; (2020); p. 143 – 153;,
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

As a common heterocyclic compound, it belong chiral-nitrogen-ligands compound,N1,N2-Dimethylethane-1,2-diamine,110-70-3,Molecular formula: C4H12N2,mainly used in chemical industry, its synthesis route is as follows.,110-70-3

A solution of N,N?-dimethylethylenediamine (1.72g, 20mmol) in dry tetrahydrofuran (60mL) was treated with 2-chloromethylpyridine hydrochloride (6.604g, 40mmol) and triethylamine (8.093g, 80mmol) and the mixture was stirred under reflux for 18h. The resulting mixture was cooled to in ice and the triethylamine hydrobromide was removed by filtration. The filtrate was then treated with 10mL 15% NaOH solution and extracted with CH2Cl2 (3¡Á40mL). The combined extracts were dried over anhydrous MgSO4. Removal of the solvent with rotary evaporator yielded dark brown oil which was chromatographed on alumina and eluted with 95/5 (v/v) mixture of ethyl acetate/MeOH (Rf=0.81). The purified ligand was obtained as yellow viscous oil (yield: 4.2g, 79%). Selected IR bands (cm-1): nu(C-H) 3064 (w), 2949 (m), 2802 (m); pyridyl groups: 1592 (s), 1577 (m), 1474 (m), 1435 (s). 1H NMR: 8.43 (m, 2H), 7.70 (m, 2H), 7.37 (m, 2H), 7.72 (m, 2H), 3.58 (s, 4H), 2.51 (s, 4H), 2.14 (s, 6H); 13C NMR: 159.74 (2-py), 149.06 (6-py), 136.78 (4-py), 123.01 (3-py), 122.42 (5-py), 63.95 (N-CH2-py), 35.40 (-CH2-CH2-N), 42.94 (CH3-N), 40.60 (CH3-N).

With the synthetic route has been constantly updated, we look forward to future research findings about N1,N2-Dimethylethane-1,2-diamine,belong chiral-nitrogen-ligands compound

Reference£º
Article; Mautner, Franz A.; Koikawa, Masayuki; Mikuriya, Masahiro; Harrelson, Emily V.; Massoud, Salah S.; Polyhedron; vol. 59; (2013); p. 17 – 22;,
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

As a common heterocyclic compound, it belong chiral-nitrogen-ligands compound,N1,N2-Dimethylethane-1,2-diamine,110-70-3,Molecular formula: C4H12N2,mainly used in chemical industry, its synthesis route is as follows.,110-70-3

General procedure: CD-1 to CD-9 were synthesized according to the procedure reported in Ref. [18]; a representative synthesis is shown in Scheme 2. Nucleophilic substitution of mono(6-O-p- tolylsulfonyl)-beta-CD (6.4459 g, 5 mmol) with the corresponding amine (25 mmol) was performed by reaction in anhydrous dimethylformamide (DMF) at 80 C in a nitrogen atmospherefor 24.0 h, followed by cooling to room temperature. (S)-Prolinamide and (R)-prolinamide were reduced with LiAlH4 to (S)-2-aminomethylpyrrolidine and (R)-2- aminomethylpyrrolidine.

With the synthetic route has been constantly updated, we look forward to future research findings about N1,N2-Dimethylethane-1,2-diamine,belong chiral-nitrogen-ligands compound

Reference£º
Article; Zhu, Qingying; Shen, Haimin; Yang, Zhujin; Ji, Hongbing; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 37; 8; (2016); p. 1227 – 1234;,
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

As a common heterocyclic compound, it belong chiral-nitrogen-ligands compound,N1,N2-Dimethylethane-1,2-diamine,110-70-3,Molecular formula: C4H12N2,mainly used in chemical industry, its synthesis route is as follows.,110-70-3

2, phosphorus trichloride (27.5g, 0.2mol) and triethylamine (40.5g, 0.4mol) was dissolved in 200mL n-hexane, the solution was placed in an ice water bath cooled to 0-5 C;N,N-dimethylethylenediamine (17.6 g, 0.2 mol) was slowly added dropwise to the solution under stirring.Hexane solution; after the addition is complete, the ice water bath is removed, and the temperature is naturally raised to room temperature, continue to react 4h; reaction is over, filter, collect the filtrate, after testing,Which contains the product of formula (III) wherein both R groups in formula (III) are methyl;

With the synthetic route has been constantly updated, we look forward to future research findings about N1,N2-Dimethylethane-1,2-diamine,belong chiral-nitrogen-ligands compound

Reference£º
Patent; Wanhua Chemical Group Co., Ltd.; Lv Yingdong; Zhu Longlong; Liu Junxian; Song Mingyan; Xue Yongyong; Li Jinming; Zhang Tao; Li Yuan; (10 pag.)CN107915758; (2018); A;,
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

As a common heterocyclic compound, it belong chiral-nitrogen-ligands compound,N1,N2-Dimethylethane-1,2-diamine,110-70-3,Molecular formula: C4H12N2,mainly used in chemical industry, its synthesis route is as follows.,110-70-3

A mixture of 2-(3-bromo-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (600 mg, 1.7 mmol), N,N’-dimethyl-ethane-1,2-diamine (0.37 mL, 3.4 mmol), copper(I) iodide (96 mg, 0.5 mmol), N,N-dimethylglycine hydrochloride (140 mg, 1.0 mmol) and potassium carbonate (923 mg, 6.7 mmol) in dimethyl sulfoxide (5 mL) was stirred at 120 C. for 16 h. Then the reaction mixture cooled to room temperature. The reaction mixture was extracted with ethyl acetate (2¡Á150 mL), washed with water (2¡Á50 mL) and saturated aqueous ammonium chloride solution (2¡Á50 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by Waters automated flash system (column: Xterra 30 mm¡Á100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 3,3-dimethyl-2-{3-[methyl-(2-methylamino-ethyl)-amino]-phenyl}-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (500 mg, 80%) as a white solid: LC/MS m/e calcd for C22H29N3O2 (M+H)+: 368.50, observed: 368.1.

With the synthetic route has been constantly updated, we look forward to future research findings about N1,N2-Dimethylethane-1,2-diamine,belong chiral-nitrogen-ligands compound

Reference£º
Patent; Chen, Li; Feng, Lichun; Huang, Mengwei; Liu, Yongfu; Wu, Guolong; Wu, Jim Zhen; Zhou, Mingwei; US2011/257151; (2011); 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

As a common heterocyclic compound, it belong chiral-nitrogen-ligands compound,N1,N2-Dimethylethane-1,2-diamine,110-70-3,Molecular formula: C4H12N2,mainly used in chemical industry, its synthesis route is as follows.,110-70-3

o-Anisaldehyde (10.0 g, 73.4 mmol, 1.0 equiv) was dissolved in EtOH (150 mL) at 25 CC, MAT-dimemylethylenediamine (8.70 mL, 80.8 mmol, 1.1 equiv) was added, and the reaction contents were stirred at 25 C for 24 h before being filtered through a pad of MgS04 and concentrated to afford the desired imidazolidine (15.0 g, 99% yield) as a white solid. Without any additional purification, this material (15.0 g, 72.8 mmol, 1.0 equiv) was dissolved in Et20 (250 mL) and cooled to -40 C. f-BuLi (1.7 M in pentane. 100 mL 170 mmol, 2.34 equiv) was then added dropwise over 1 h at -40 C. Upon completion, the resultant orange reaction contents were warmed slowly to -20 C. stirred for an additional 7 h, and then transferred by cannula over 5 min into a flask containing (CBrCl2)2 (55.3 g, 170 mmol, 2.34 equiv) in Et20 (250 mL) at 0 C. The reaction contents were then stirred for 12 h, during which time they were warmed to 25 C; upon completion, the solution was recooled to 0 C and 1 M HCI (500 mL) was added slowly. The resultant solution was stirred for 1 h at 0 C, quickly warmed to 25 C, and then quenched by the addition of water (500 mL). The reaction contents were then extracted with EtOAc (3 x 250 mL), and the combined organic extracts were washed with water (500 mL) and brine (250 mL). dried (MgSO-i), and 73 concentrated.’23’ The resultant crude yellow solid was purified by flash column chromatography (silica gel, hexanes EtOAc, 9/1) to give the desired brominated product 28 (8.12 g, 52% yield) as a white solid. This material (8.12 g, 37.8 mmol, 1.0 equiv) was suspended in MeOH (100 mL) at 25 C and cooled to 0 C. NaBHj (2.88g , 75.6 mmol, 2.0 equiv) was added portionwise and the reaction contents were stirred for 1 h at 0 C. Upon completion, the reaction contents were quenched with water (100 mL) and concentrated. The reaction contents were redissolved in EtOAc ( 100 mL), poured into water (100 mL), and extracted with EtOAc (3 x 50 mL). The combined organic extracts were washed with water ( 150 mL) and brine (50 mL), dried (MgSO- , and concentrated to afford the desired alcohol (7.83 g, 96%) as a white solid. Pressing forward without any additional purification, this newly prepared material (7.83 g, 36.1 mmol, 1.0 equiv) was dissolved in EtjO (180 mL) and pyridine (0.437 mL, 5.41 mmol, 0.15 equiv) and PBr^ (3.41 mL, 36.1 mmol, 1.0 equiv) were added sequentially at 25 C. The reaction contents were then stirred for 4 h at 25 C. Upon completion, the reaction contents were quenched by the addition of water (100 mL), poured into water ( 100 ml), and extracted with EtOAc (3 x 150 mL). The combined organic extracts were washed with water (200 mL) and brine (100 mL), dried (MgS04), and concentrated to give the desired bromide (10.0 g, 99%) as a white solid. [Note: This product quickly decomposes on standing once it is neat and should be carried forward immediately. | Finally, KHMDS (0.5 M in toluene, 129 mL, 64.5 mmol, 1.8 equiv) was added to a solution of diethyl phosphite (9.19 mL, 71.4 mmol, 2.0 equiv) in THF (100 mL) at 0 C and stirred for 15 min. To this solution was added dropwise a solution of the freshly prepared bromide (10.0 g, 35.7 mmol, 1.0 equiv) dissolved in THF (100 mL), and the reaction contents were stirred for 12 h with slow warming to 25 C. Upon completion, the reaction contents were quenched with saturated NH4CI (150 mL), poured into water (150 mL), and extracted with EtOAc (3 x 150 mL). The combined organic extracts were washed with water (100 mL) and brine (100 mL), dried (MgS04), and concentrated to give the phosphonate 31 (10.79 g, 90%) as a colorless oil. 31: R/ = 0.21 (silica gel, EtOAc); IR (film) vmax 2981, 1589, 1572, 1466, 1435, 1267, 1082, 965, 864, 771 ; NMR (400 MHz, CDCI3) delta 7.18 (d, / = 8.0 Hz, 1 H), 7.07 (app dt, J = 8.0, 2.4 Hz, 1 H), 6.81 (d, J = 8.4 Hz, 1 H), 4.05 (dq, J = 7.2, 7.2 Hz, 4 H), 3.85 (s, 3 H), 3.50 (d, J = 22.0 Hz, 2 H), 1.26 (t, J = 7.2 Hz, 6 H); l3C NMR (75 MHz, CDCI3) delta 158.4 (d, J = 5.4 Hz). 128.6 (d, J = 3.8 Hz), 125.8 (d, J = 7.5 Hz), 125.0 (d, J = 3.5 Hz), 121.6 (d, J = 10.6 Hz), 109.4 (d, J = 3.4 Hz), 61.9 (d, J = 6.5 Hz), 55.9, 28.3 (d, J = 139.0 Hz), 16.3 (d, J = 6.4 Hz); HRMS (MALDI-FTMS) calcd for Ci2H|9BrP04+ [M + H*] 337.0204, found 337.0189

With the synthetic route has been constantly updated, we look forward to future research findings about N1,N2-Dimethylethane-1,2-diamine,belong chiral-nitrogen-ligands compound

Reference£º
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; SNYDER, Scott Alan; SHERWOOD, Trevor C.; ROSS, Audrey G.; OH, Hyunju; GHOSH, Sankar; WO2011/103442; (2011); A2;,
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

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO266,mainly used in chemical industry, its synthesis route is as follows.,110-70-3

A solution of di-tert-butyl dicarbonate (4.95 g, 22.69 mmol) in CH2Cl2 (240 mL) was added dropwise to a stirred solution of N,N?-dimethylethane-1,2-diamine (4 g, 45.38 mmol) in CH2Cl2 (80 mL) over a period of 20h. The resulting mixture was stirred at r.t. for 3h. The mixture was then washed sequentially with sat. Na2CO3 (2 x 100 mL), water (50 mL), and sat. brine (50 mL). The organic solution was dried (MgSO4) and concentrated in vacuo. Purification by FCC, eluting with 0-10% CH3OH in CH2Cl2 gave the title compound (2.177 g, 51%) as a pale yellow oil; 1H NMR: 1.40 (9H, s), 2.28 (3H, s), 2.57 (2H, t), 2.79 (3H, s), 3.20 (2H, t).

With the synthetic route has been constantly updated, we look forward to future research findings about N1,N2-Dimethylethane-1,2-diamine,belong chiral-nitrogen-ligands compound

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; FINLAY, Maurice, Raymond, Verschoyle; WARD, Richard, Andrew; KADAMBAR, Vasantha, Krishna; CHANDRASHEKAR, Reddy, C.; MURUGAN, Andiappan; REDFEARN, Heather, Marie; WO2013/14448; (2013); 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, cas is 33527-91-2, it is a common heterocyclic compound, the chiral-nitrogen-ligands compound, its synthesis route is as follows.,33527-91-2

General procedure: LiBEt3H (1 mL, 1.0 M in THF, 1 mmol) and Me6TREN (0.26 mL,1 mmol) were added to 5 mL of hexane, precipitating a white powder.THF was slowly added dropwise with stirring until a homogeneoussolution was obtained (approx. 3 mL) Cooling of the solutionat 30 C yielded X-ray quality colorless crystals

With the synthetic route has been constantly updated, we look forward to future research findings about Tris[2-(dimethylamino)ethyl]amine,belong chiral-nitrogen-ligands compound

Reference£º
Article; Kennedy, Alan R.; McLellan, Ross; McNeil, Greg J.; Mulvey, Robert E.; Robertson, Stuart D.; Polyhedron; vol. 103; (2016); p. 94 – 99;,
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

As a common heterocyclic compound, it belong chiral-nitrogen-ligands compound,Tris[2-(dimethylamino)ethyl]amine,33527-91-2,Molecular formula: C12H30N4,mainly used in chemical industry, its synthesis route is as follows.,33527-91-2

Embodiment 5Production of [Cu(Me6tren)]BPh4 0.20 g (0.87 mmol) Me6tren (1) was dissolved in approx. 2 ml acetone and a solution of 0.30 g (0.81 mmol) [Cu(CH3CN)4]PF6 (tetrakis(acetonitrile)copper(I)-hexafluorophosphate) in approx. 4 ml acetone was added slowly under constant stirring. A solution of 0.28 g (0.82 mmol) NaBPh4 (sodium tetraphenylborate) in approx. 2 mL acetone was added subsequently to the colorless, complex solution thus obtained, for the replacement of anions. For the preparation of the solid, the complex solution was added to 20 ml diethylether. The voluminous solid of [Cu(Me6tren)]BPh4 (10) obtained was dried in vacuum. 0.48 g (96.6%) of a colorless powder was obtained as the product.All work was carried out in an argon box. It is possible, however, to carry out all work with the Schlenk technique under argon or nitrogen as well.The complex [Cu(Me6tren)]BPh4 is shown in FIG. 1.The results of the crystal structure analysis of [Cu(Me6tren)]BPh4 are shown in FIG. 2.

With the synthetic route has been constantly updated, we look forward to future research findings about Tris[2-(dimethylamino)ethyl]amine,belong chiral-nitrogen-ligands compound

Reference£º
Patent; Schindler, Siegfried; Wuertele, Christian; US2012/16127; (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

As a common heterocyclic compound, it belong chiral-nitrogen-ligands compound,Tris[2-(dimethylamino)ethyl]amine,33527-91-2,Molecular formula: C12H30N4,mainly used in chemical industry, its synthesis route is as follows.,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.

With the synthetic route has been constantly updated, we look forward to future research findings about Tris[2-(dimethylamino)ethyl]amine,belong chiral-nitrogen-ligands compound

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