Category: quinuclidine

Quinuclidine-4-carboxylic acid hydrochloride, cas is 40117-63-3, it is a common heterocyclic compound, the quinuclidine compound, its synthesis route is as follows.,40117-63-3

1. Preparation of 3-fluorobenzyl quinuclidine-4-carboxylate (Compound 91). A mixture of quinuclidine-4-carboxylic acid hydrochloride (100 mg, 0.52 mmol) and thionyl chloride (500 mul, 6.85 mmol) was refluxed for 2 hours. The reaction was cooled to room temperature, and the solvent was accurately removed. The residue was suspended in dry DCM and treated with (3-fluorophenyl)methanol (65.8 mg, 0.52 mmol). The reaction was stirred at room temperature for 24 hours. The solvent was evaporated, and the residue was dissolved in water (1 ml), basified with NaHCO3 and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and evaporated to obtain 3-fluorobenzyl quinuclidine-4-carboxylate (41 mg, 29.8% yield), which was used in the next step without any further purification.

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Reference£º
Patent; Chiesi Farmaceutici S.p.A.; US2012/276018; (2012); A1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

It is a common heterocyclic compound, the quinuclidine compound, Ethyl quinuclidine-4-carboxylate, cas is 22766-68-3 its synthesis route is as follows.,22766-68-3

1-azabicyclo[2.2.2]oct-4-yl]bis(4-fluorophenyl)]methanol A solution of 4-fluorophenylmagnesiumbromide (1.0 M in THF, 4.4 mL, 4.4 mmol) was chilled down to 0 C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.1973 g, 1.08 mmol) in THF (4 mL) was slowly added to the reaction mixture at 0 C. over 20 min. The reaction was allowed to warm up to room temperature and then heated at 60 C. for 16 h. The reaction was chilled in an ice bath, quenched with saturated NH4Cl, and concentrated under vacuum. The resulting residue was treated with H2O and extracted with EtOAc. The combined organic layers were dried with MgSO4, filtered, and concentrated under vacuum to yield the desired product (0.3152 g, 88.9%). EI-MS m/z 330(M+H+) Rt (1.65 min).

As the rapid development of chemical substances, we look forward to future research findings about 22766-68-3

Reference£º
Patent; Laine, Damane I.; Palovich, Michael R.; McCleland, Brent W.; Neipp, Christopher E.; Thomas, Sonia M.; US2007/185155; (2007); A1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

It is a common heterocyclic compound, the quinuclidine compound, Ethyl quinuclidine-4-carboxylate, cas is 22766-68-3 its synthesis route is as follows.,22766-68-3

1 Azabicyclo 2.2.2Joct-4 yl(diphe yl)methanol ;A solution of phenyllithium (1.5-1.7 M in 70 cyclohexane / 30 ether, 20.0 mL, 32 mmol) was chilled down to -30 C under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4- carboxylate (1.51g, 8.23 mmol) in THF (20 mL) was slowly added to the reaction mixture at -30 C over 25 min. The reaction was allowed to warm up to room temperature overnight. The reaction was quenched with H20 and then evaporated to dryness under vacuum. H20 and EtOAc were added, causing a white solid to crash out. This solid was filtered off, to give the title compound (0.79 g). The aqueous phase was further extracted with EtOAc, the combined organic layers were dried over MgS04, filtered, and concentrated under vacuum. The crude product was treated with EtOAc and hexane and filtered to yield more of the title compound (0.67 g). Total yield (1.46 g, 60.7%). EI-MS m/z 294 (M+H+) Rt (1.37 min).

As the rapid development of chemical substances, we look forward to future research findings about 22766-68-3

Reference£º
Patent; GLAXO GROUP LIMITED; WO2005/112644; (2005); A2;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

Quinuclidine-4-carboxylic acid hydrochloride, cas is 40117-63-3, it is a common heterocyclic compound, the quinuclidine compound, its synthesis route is as follows.,40117-63-3

Under the protection of nitrogen, phenyllithium (1.5 – 1.7M cyclohexane/diethyl ether solution (70:30), 30.0 ml, 48.00mmol) solution cooled to -30 C, in -30 C under, 0.5 hours slowly dropping WD2 (2.27g, 12 . 35mmol) of THF (30 ml) solution to the reaction mixture. The reaction liquid heating to room temperature reaction 16 hours, adding water quenching reaction, mixed solution under vacuum to evaporate to dry, adding water and ethyl acetate, to obtain white solid to settle out, filtering to obtain solid, shall WD1 (1.19g). The aqueous phase is further extracted with ethyl acetate, the combined organic layer was dried with anhydrous sodium sulfate, filtered, concentrated under reduced pressure to get the crude product, the crude product of ethyl acetate and hexane processing, filtering to obtain WD1.

40117-63-3 is used more and more widely, we look forward to future research findings about Quinuclidine-4-carboxylic acid hydrochloride

Reference£º
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Yi Shixu; Fu Li; (6 pag.)CN106810546; (2017); A;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

Ethyl quinuclidine-4-carboxylate, cas is 22766-68-3, it is a common heterocyclic compound, the quinuclidine compound, its synthesis route is as follows.,22766-68-3

Step 1. A solution of 4-carbethoxyquinuclidine (10.92 g) in THF (155 mL) was treated at-780C with borane-THF (1.0 M, 77.5 mL). The resulting mixture was stirred at -78C for 4 h, then treated with water (50 mL), warmed to room temperature and stirred for an additional hour. The reaction mixture was diluted with ethyl acetate and the aqueous phase was separated and extracted with two further portions of ethyl acetate. The combined organic layers were washed with brine- (twice), dried (MgSO4), filtered and evaporated in vacuo. Purification by silica gel chromatography (eluting with cyclohexane-ethyl acetate [1 :0 to 1 :1]) gave 1-boranyl-1-aza-bicyclo[2.2.2]octane-4- carboxylic acid ethyl ester (7.12 g, 61%) as an off-white solid. 1H NMR (400 MHz, CDCI3) delta 4.16 (2H1 q, J = 6.9), 3.10-3.05 (6H1 m), 1.98-1.93 (6H, m), 1.26 (3H, t, J = 6.9).

22766-68-3 is used more and more widely, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate

Reference£º
Patent; ARGENTA DISCOVERY LIMITED; WO2008/99186; (2008); A1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

Ethyl quinuclidine-4-carboxylate, cas is 22766-68-3, it is a common heterocyclic compound, the quinuclidine compound, its synthesis route is as follows.,22766-68-3

Example 13: Preparation of 4-[cyano(di-2-thienyl)methyl]-1-[3- (DhenVIoxVlDroDVIl-1-azoniabicvclo [2.2.210ctane bromide;. 1-Azabicyclof2. 2. 2 Joct-4-yl(di-2-thienyl)methanol; A solution of 2-thienyllithium (1.0 M in THF, 13.0 mL, 13 mmol) was chilled down to -30 C under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.77 g, 4.20 mmol) in THF (12 mL) was slowly added to the 2-thienyllithium at-30 C over 40 min. The reaction was allowed to warm up to room temperature for overnight. The reaction was quenched with H20 and then diluted with EtOAC, hexane and DCM causing a solid to crash out of solution. The solid was filtered off, resulting in the desired compound (0.9132 g, 71.3%). EI-MS m/z 306 (M+) Rt (1.33 min).

22766-68-3 is used more and more widely, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate

Reference£º
Patent; GLAXO GROUP LIMITED; WO2005/112644; (2005); A2;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

Quinuclidine-4-carboxylic acid hydrochloride, cas is 40117-63-3, it is a common heterocyclic compound, the quinuclidine compound, its synthesis route is as follows.,40117-63-3

Step 4. Quinuclidin-4-ylcarbonyl chloride hydrochloride Quinuclidine-4-carboxylic acid hydrochloride (0.192 g, 0.001 mole) was suspended in dichloromethane (5 ml) and dimethylformamide (1 drop) and oxalyl chloride (0.436 ml. 0.635 g, 0.005 mole) were added. The resulting suspension was heated to reflux under an atmosphere of argon for six hours. Following concentration of the suspension in vacuo the residue was suspended in dichloromethane, concentrated in vacuo and finally dried in vacuo to give the title compound as a pale brown solid.

40117-63-3 is used more and more widely, we look forward to future research findings about Quinuclidine-4-carboxylic acid hydrochloride

Reference£º
Patent; SmithKline Beecham p.l.c.; US6281226; (2001); B1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

Quinuclidine-4-carboxylic acid hydrochloride, cas is 40117-63-3, it is a common heterocyclic compound, the quinuclidine compound, its synthesis route is as follows.,40117-63-3

Under the protection of nitrogen, a solution for dissolving the WD2 with the tetrahydrofuran is added into a 20-liter reaction kettle, the temperature is controlled to be below 40 C under stirring, and 3.8 liters of phenylmagnesium bromide reagent is added dropwise, and carrying out heating reflux reaction for 4 hours. The temperature is controlled to be controlled at 40 C under cooling and stirring, and 1.547 kg of ammonium chloride aqueous solution (25%) is added dropwise) after dropwise adding, adding about 74 kg of purified water, and standing for liquid separation after stirring, so as to obtain an organic phase; extracting the water phase by using 2-methyl tetrahydrofuran, the organic phase is combined with the organic phase, and the organic phase is washed with a 25% sodium chloride aqueous solution. A 1 m hydrochloric acid aqueous solution is added to the obtained organic phase to be about 140Kg, fully stirring, standing and separating liquid to obtain a water phase; dropwise adding a sodium hydroxide aqueous solution with the concentration of 4 m into the obtained hydrochloric acid salt water solution of the WD1 to adjust the pH value, and separating out solids. After dropping, stirring is continued for about 0.5 hour, and the mixture is filtered to obtain a filter cake; the filtrate is subjected to reduced pressure concentration until no large amount of distillate is discharged, and the filtrate is filtered to obtain a filter cake; combining the obtained filter cakes twice, and washing with purified water with the temperature of 25 +/-5 C, and then pulping is carried out by using purified water at 25 +/-5 C for about 2.61 kg. The filter cake is firstly washed with purified water at 25 +/-5 C, and then is dried to obtain WD1:

With the rapid development of chemical substances, we look forward to future research findings about Quinuclidine-4-carboxylic acid hydrochloride

Reference£º
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Yi Shixu; Fu Li; (6 pag.)CN106810546; (2017); A;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

Quinuclidine-4-carboxylic acid hydrochloride, cas is 40117-63-3, it is a common heterocyclic compound, the quinuclidine compound, its synthesis route is as follows.,40117-63-3

(Quinuclidin-4-yl)carboxylic acid was prepared from 4-cyanoquinuclidine (Oakwood Products) following the procedure of Grob and Renk, Helv. Chim. Acta, 37, 1681 (1954). To a stirred suspension of quinuclidine-4-carboxylic acid hydrochloride (100 mg, 0.523 mmol) in 3 mL of anhydrous tetrahydrofuran at 0 C. was added borane methylsulfide complex (42 mg, 0.553 mmol). The mixture was stirred at room temperature for 1 hr and heated to reflux overnight. The reaction was cooled to 0 C. and carefully treated with 1 mL of methanol. The solvent was then removed under reduced pressure to leave the desired alcohol. Yield 36 mg. MS (m/e): 141.

With the rapid development of chemical substances, we look forward to future research findings about Quinuclidine-4-carboxylic acid hydrochloride

Reference£º
Patent; CoMentis, Inc.; BILCER, Geoffrey M.; NG, Raymond; (104 pag.)US2016/9706; (2016); A1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider

Ethyl quinuclidine-4-carboxylate, cas is 22766-68-3, it is a common heterocyclic compound, the quinuclidine compound, its synthesis route is as follows.,22766-68-3

1-azabicyclo[2.2.2]oct-4-yl[bis(4-methylphenyl)]methanol A solution of 4-methylphenylmagnesiumbromide (1.0 M in THF, 3.3 mL, 3.3 mmol) was chilled down to 0 C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.1509 g, 0.823 mmol) in THF (4 mL) was slowly added to the reaction mixture at 0 C. over 20 min. The reaction was allowed to warm up to room temperature and then heated at 60 C. for 16 h. The reaction was chilled in an ice bath, quenched with saturated NH4Cl, and concentrated under vacuum. The resulting residue was treated with H2O and extracted with EtOAc. The combined organic layers were dried with MgSO4, filtered, and concentrated under vacuum to yield the desired product (0.2291 g, 86.6%). EI-MS m/z 322(M+H+) Rt (1.57 min).

With the rapid development of chemical substances, we look forward to future research findings about Ethyl quinuclidine-4-carboxylate

Reference£º
Patent; Laine, Damane I.; Palovich, Michael R.; McCleland, Brent W.; Neipp, Christopher E.; Thomas, Sonia M.; US2007/185155; (2007); A1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider