As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO158,mainly used in chemical industry, its synthesis route is as follows.,15529-49-4
Compound 10 (628.5 mg, 1.0 mmol) and degassed morpholine (15 mL) were placed in a 100-mL Young-Schlenk container substituted with argon gas. Thereafter, the Young-Schlenk container was placed in an oil bath, and heated to 120 C. while stirring the components in the Young-Schlenk container, thereby causing a reaction. The progress of the reaction was confirmed by TLC, and the heating was stopped after two hours. Subsequently, the morpholine in the reaction mixture restored to room temperature (25 C.) was removed after collection with a liquid nitrogen trap under reduced pressure (0.1 to 2 mmHg). At this time, the reaction mixture was sufficiently stirred, and the Young-Schlenk container was immersed in water at room temperature (25 C.) to prevent cooling of the Young-Schlenk container by the heat of vaporization. (0255) After sufficiently removing the morpholine, dichlorotris(triphenylphosphino)ruthenium (II) (958.8 mg, 1.0 mmol) and dehydrated toluene (20 mL) were added while introducing argon gas into the container, and the mixture was heated to 110 C. using an oil bath, thereby causing a reaction. The heating was stopped after two hours, and the reaction mixture was restored to room temperature (25 C.). (0256) Subsequently, dehydrated hexane (40 mL) was added to the reaction mixture in an argon gas atmosphere. Thereafter, the whole mixture, including the hexane layer and the toluene layer, in the Young-Schlenk container was stirred and completely mixed. After leaving the mixture unattended for an hour, the generated purple substance was filtered out in an argon atmosphere while being washed with dehydrated diethylether, thereby obtaining a crude product. (0257) Subsequently, the resulting crude product was subjected to column chromatography (developing solvent: chloroform/THF=10/1) in which silica gels were accumulated to about 10 cm, thereby removing a compound with high polarity. The effluent was collected to a flask and the collection was continued until the color of the purple liquid was slightly diluted. After this operation, the solution collected in the recovery flask was rapidly concentrated by an evaporator, thereby obtaining 563.7 mg (0.73 mmol, 73%) of substantially pure Compound 2f (RUPCY3) as a purple substance. (0258) The spectral data of Compound 2f (RUPCY3) is shown below. (0259) 1H NMR (600 MHz, CDCl3): delta 8.12 (d, 2H, J=8.2 Hz, C12H6N2), 7.86 (d, 2H, J=8.2 Hz, C12H6N2), 7.80 (s, 2H, C12H6N2), 4.05 (d, 4H, J 35=7.6 Hz, PCH2), 2.42-2.51 (br, 4H, C6H11), 2.31 (d, 4H, J=11.0 Hz C6H11), 2.12 (d, 4H, J=12.4 Hz, C6H11), 1.61-1.94 (m, 20H, C6H11), 1.18-1.37 (m, 12H, C6H11). 13C NMR (151 MHz, CDCl3): delta 163.6, 149.3, 132.6, 128.6, 125.3, 121.8, 41.4, (d, 1JPC=23.1 Hz) 36.6 (t, 1JPC=7.2 Hz), 30.7, 29.4, 27.8, 27.6, 26.4. 31P{1H} NMR (243 MHz, CDCl3): delta 56.8. HRMS (ESI, (M-Cl)+) Calcd for C38H54ClN2P2Ru+: 737.2494. Found m/z=737.2483. (0260) FIG. 2 shows the result of an X-ray single crystal structural analysis (Oak Ridge Thermal Ellipsoid Plot) of Compound 2f.
With the complex challenges of chemical substances, we look forward to future research findings about Dichlorotris(triphenylphosphino)ruthenium (II),belong ruthenium-catalysts compound
Reference£º
Patent; National University Corporation Nagoya University; Saito, Susumu; Noyori, Ryoji; Miura, Takashi; Naruto, Masayuki; Iida, Kazuki; Takada, Yuki; Toda, Katsuaki; Nimura, Sota; Agrawal, Santosh; Lee, Sunkook; (42 pag.)US9463451; (2016); B2;,
Highly efficient and robust molecular ruthenium catalysts for water oxidation
Catalysts | Special Issue : Ruthenium Catalysts – MDPI