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CAS No. : | 1435-55-8 | MDL No. : | MFCD00135599 |
Formula : | C20H26N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 326.43 | Pubchem ID : | - |
Synonyms : |
(+)-Hydroquinidine;Hydroconquinine;Dihydroquinidine;Hydroquinidine
|
Num. heavy atoms : | 24 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.55 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 100.21 |
TPSA : | 45.59 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.07 cm/s |
Log Po/w (iLOGP) : | 3.17 |
Log Po/w (XLOGP3) : | 3.13 |
Log Po/w (WLOGP) : | 2.69 |
Log Po/w (MLOGP) : | 2.31 |
Log Po/w (SILICOS-IT) : | 3.12 |
Consensus Log Po/w : | 2.89 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.88 |
Solubility : | 0.043 mg/ml ; 0.000132 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.76 |
Solubility : | 0.0572 mg/ml ; 0.000175 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.65 |
Solubility : | 0.00726 mg/ml ; 0.0000222 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 4.3 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302-H312-H332 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With palladium 10% on activated carbon; hydrogen; In methanol; under 2280.15 Torr; for 5h; | Weigh quinidine (30.83 mmol) shown in Formula IV in a hydrogenation reactor, add 50 mL of methanol to dissolve it, and then add 10% palladium / carbon catalyst (32.89 mmol). After the reactor was replaced three times with argon, it was reacted for 5 h under 3 atm hydrogen. The catalyst was removed by filtration, and the filtrate obtained by the filtration was concentrated to obtain a crude product. The crude product was dissolved in dichloromethane (150 mL), and then the obtained dichloromethane solution was extracted with water (3 × 80 mL) (whether it was washed), The washed methylene chloride solution was dried with anhydrous sodium sulfate, and concentrated under reduced pressure to obtain dihydroquinidine represented by formula III. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8.6 g (52.7%) | Preparation of dihydroquinidine by catalytic reduction of quinidine To a solution of 16.2 g of quinidine (0.05 mol) in 150 mL of 10% H2 SO4 (15 g conc H2 SO4 in 150 mL H2 O) was added 0.2 g of PdCl2 (0.022 eq; 0.0011 mol). The reaction mixture was hydrogenated in a Parr shaker at 50 psi pressure. After 2h, the catalyst was removed by filtration through a pad of celite and washed with 150 mL of water. The faint yellow solution so obtained was slowly added to a stirred aqueous NaOH solution (15 g of NaOH in 150 mL H2 O. A white precipitate immediately formed and the pH of the solution was brought to 10-11 by addition of excess aqueous 15% NaOH. The precipitate was collected by filtration, pressed dry and suspended in ethanol (175 mL). The boiling solution was quickly filtered and upon cooling to room temperature, white needles crystallized out. The crystals were collected and dried under vacuum (90 C.; 0.05 mm Hg) overnight. This gave 8.6 g (52.7%) of pure dihydroquinidine mp=169.5-170 C. The mother liquor was placed in a freezer at -15 C. overnight. After filtration and drying of the crystals, another 4.2 g (21.4%) of pure material was obtained, raising the total amount of dihydroquinidine to 12.8 g (74.1%). | |
8.6 g (52.7%) | Preparation of dihydroquinidine by catalytic reduction of quinidine To a solution of 16.2 g of quinidine (0.05 mol) in 150 mL of 10% H2 SO4 (15 g conc H2 SO4 in 150 mL H2 O) was added 0.2 g of PdCl2 (0.022 eq; 0.0011 mol). The reaction mixture was hydrogenated in a Parr shaker at 50 psi pressure. After 2 h, the catalyst was removed by filtration through a pad of celite and washed with 150 mL of water. The faint yellow solution so obtained was slowly added to a stirred aqueous NaOH solution (15 g of NaOH in 150 mL H2 O. A white precipitate immediately formed and the pH of the solution was brought to 10-11 by addition of excess aqueous 15% NaOH. The precipitate was collected by filtration, pressed dry and suspended in ethanol (175 mL). The boiling solution was quickly filtered and upon cooling to room temperature, white needles crystallized out. The crystals were collected and dried under vacuum (90 C.; 0.05 mm Hg) overnight. This gave 8.6 g (52.7%) of pure dihydroquinidine mp=169.5-170 C. The mother liquor was placed in a freezer at -15 C. overnight. After filtration and drying of the crystals, another 4.2 g (21.4%) of pure material was obtained, raising the total amount of dihydroquinidine to 12.8 g (74.1%). | |
8.6 g (52.7%) | Preparation of dihydroquinidine by catalytic reduction of quinidine To a solution of 16.2 g of quinidine (0.05 mol) in 150mL of 10% H2 SO4 (15 g conc H2 SO4 in 150mL H2 O) was added 0.2 g of PdCl2 (0.022 eq; 0.0011 mol). The reaction mixture was hydrogenated in a Parr shaker at 50 psi pressure. After 2h, the catalyst was removed by filtration through a pad of celite and washed with 150mL of water. The faint yellow solution so obtained was slowly added to a stirred aqueous NaOH solution (15 g of NaOH in 150mL H20. A White precipitate immediately formed and the pH of the solution was brought to 10-11 by addition of excess aqueous 15% NaOH. The precipitate was collected by filtration, pressed dry and suspended in ethanol (175mL). The boiling solution was quickly filtered and upon cooling to room temperature, white needles crystallized out. The crystals were collected and dried under vacuum (90 C.; 0.05 mm Hg) overnight. This gave 8.6 g (52.7%) of pure dihydroquinidine mp=169.5-170 C. The mother liquor was placed in a freezer at 15 C. overnight. After filtration and drying of the crystals, another 4.2 g (21.4%) of pure material was obtained, raising the total amount of dihydroquinidine to 12.8 g (74.1%). |
8.6 g (52.7%) | Preparation of Dihydroquinidine by Catalytic Reduction of Quinidine To a solution of 16.2 g of quinidine (0.05 mol) in 150 mL of 10% H2 SO4 (15 g conc H2 SO4 in 150 mL H2 O) was added 0.2 g of PdCl2 (0.022 eq; 0.0011 mol). The reaction mixture was hydrogenated in a Parr shaker at 50 psi pressure. After 2 h, the catalyst was removed by filtration through a pad of celite and washed with 150 mL of water. The faint yellow solution so obtained was slowly added to a stirred aqueous NaOH solution (15 g of NaOH in 150 mL H2 O. A white precipitate immediately formed and the pH of the solution was brought to 10-11 by addition of excess aqueous 15% NaOH. The precipitate was collected by filtration, pressed dry and suspended in ethanol (175 mL). The boiling solution was quickly filtered and upon cooling to room temperature, white needles crystallized out. The crystals were collected and dried under vacuum (90 C.; 0.05 mm Hg) overnight. This gave 8.6 g (52.7%) of pure dihydroquinidine mp=169.5-170 C. The mother liquor was placed in a freezer at 15 C. overnight. After filtration and drying of the crystals, another 4.2 g (21.4%) of pure material was obtained, raising the total amount of dihydroquinidine to 12.8 g (74.1%). | |
8.6 g (52.7%) | EXAMPLE 4 Preparation of dihydroquinidine derivative Preparation of dihydroquinidine by catalytic reduction of quinidine To a solution of 16.2 g of quinidine (0.05 mol) in 150 mL of 10% H2 SO4 (15 g conc H2 SO4 in 150mL H2 O) was added 0.2 g of PdCl2 (0.022eq; 0.0011 mol). The reaction mixture was hydrogenated in a Parr shaker at 50 psi pressure. After 2 h, the catalyst was removed by filtration through a pad of celite and washed with 150 mL of water. The faint yellow solution so obtained was slowly added to a stirred aqueous NaOH solution (15 g of NaOH in 150 mL H2 O. A white precipitate immediately formed and the pH of the solution was brought to 10-11 by addition of excess aqueous 15% NaOH. The precipitate was collected by filtration, pressed dry and suspended in ethanol (175 mL). The boiling solution was quickly filtered and upon cooling to room temperature, white needles crystallized out. The crystals were collected and dried under vacuum (90 C.; 0.05 mm Hg) overnight. This gave 8.6 g (52.7%) of pure dihydroquinidine mp=169.5-170 C. The mother liquor was placed in a freezer at 15 C. overnight. After filtration and drying of the crystals, another 4.2 g (21.4%) of pure material was obtained, raising the total amount of dihydroquinidine to 12.8 g (74.1%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In dichloromethane; | From <strong>[1435-55-8]di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong></strong> To a 0 C. solution of 1.22 g <strong>[1435-55-8]di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong></strong> (0.0037 mol) in 30 mL of CH2 Cl2 was added 0.78 mL of Et3 N (0.0056 mol; 1.5 eq), followed by 0.71 mL of p-chlorobenzoyl chloride (0.005 mol; 1.2 eq) in 1 mL CH2 Cl2. After stirring 30 minutes at 0 C. and 1 hour at room temperature, the reaction was quenched by the addition of 10% Na2 CO3 (20 mL). After separation, the aqueous layer was extracted with three 10 mL portions of CH2 Cl2. The combined organic layers were dried over Na2 SO4 and the solvent removed under vacuum. The crude product was purified as described above. Di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong> p-chlorobenzoate (1) was obtained in 91% yield (1.5 g) as a white foam. |
91% | In dichloromethane; | From <strong>[1435-55-8]di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong></strong> To a 0 C. solution of 1.22g <strong>[1435-55-8]di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong></strong> (0.0037 mol) in 30mL of CH2 Cl2 was added 0.78mL of Et3 N (0.0056 mol; 1.5 eq), followed by 0.71mL of p-chlorobenzoyl chloride (0.005 mol; 2 eq) in 1mL CH2 Cl2 After stirring 30 minutes at 0 C. and 1 hour at room temperature, the reaction was quenched by the addition of 10% Na2 CO3 (20mL). After separation, the aqueous layer was extracted with three 10mL portions of CH2 Cl2. The combined organic layers were dried over Na2 S04 and the solvent removed under vacuum. The crude product was purified as described above. Di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong> p-chlorobenzoate (1) was obtained in 91% yield (1.5g) as a white foam. |
91% | In dichloromethane; | From <strong>[1435-55-8]di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong></strong> To a 0 C. solution of 1.22 g <strong>[1435-55-8]di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong></strong> (0.0037 mol) in 30 mL of CH2 Cl2 was added 0.78 mL of Et3 N (0.0056 mol; 1.5 eq). followed by 0.71 mL of p-chlorobenzoyl chloride (0.005 mol; 1.2 eq) in 1 mL CH2 Cl2. After stirring 30 minutes at 0 C. and 1 hour at room temperature, the reaction was quenched by the addition of 10% Na2 CO3 (20 mL). After separation, the aqueous layer was extracted with three 10 mL portions of CH2 Cl2. The combined organic layers were dried over Na2 SO4 and the solvent removed under vacuum. The crude product was purified as described above. Di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong> p-chlorobenzoate (1) was obtained in 91% yield (1.5 g) as a white foam. |
91% | In dichloromethane; | From <strong>[1435-55-8]di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong></strong> To a 0 C. solution of 1.22 g <strong>[1435-55-8]di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong></strong> (0.0037 mol) in 30 mL of CH2 Cl2 was added 0.78 mL of Et3 N (0.0056 mol; 1.5 eq), followed by 0.71 mL of p-chlorobenzoyl chloride (0.005 mol; 1.2 eq) in 1 mL CH2 Cl2. After stirring 30 minutes at 0 C. and 1 hour at room temperature, the reaction was quenched by the addition of 10% Na2 CO3 (20 mL). After separation, the aqueous layer was extracted with three 10 mL portions of CH2 Cl2. The combined organic layers were dried over Na2 SO4 and the solvent removed under vacuum. The crude product was purified as described above. Di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong> p-chlorobenzoate (1) was obtained in 91% yield (1.5g) as a white foam. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With sodium hydroxide; triethylamine; In dichloromethane; | EXAMPLE 23 Synthesis of Methylphenylcarbamoyl <strong>[1435-55-8]di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong></strong> (MPC-DHQD) Di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong> (1.4 g, 4.3 mmol, 1 eq) was dissolved in 15 ml of CH2 Cl2 under nitrogen atmosphere in a 3-necked 100 ml round bottom flask. At room temperature, 2 ml of triethylamine (14.4 mmol, 3.3 eq) was added to the solution and stirred for 30 minutes. N-methyl-N-phenylcarbamoyl chloride (1.6 g, 9.4 mmol, 2.2 eq) was dissolved in 6 ml CH2 Cl2 and added to the reaction mixture dropwise via an addition funnel. The reaction mixture was stirred under N2 for three days before reaching reaction completion. 50 ml of 2N NaOH were added, and the phases were separated. The CH2 Cl2 layer was saved, and the aqueous phase was extracted with 50 ml of CH2 Cl2. The CH2 Cl2 phases were combined and dried over MgSO4 before being concentrated down to afford a gummy pink material. Purification via flash chromatography (silica gel, 95.5 EtOAc/Et3 N, v/v) afforded a yellow material which was then crystallized from CH3 CN to obtain white starlike crystals (1.27 g, 65% yield). Characterization: mp. 119-120 C. High resolution mass spec; calculated molecular mass--459.25217 amu, found--459.2519 amu. 1 H NMR (300 MHz, CDCl3 with TMS); 8.7 delta (d, 1H), 8.0 delta (d,1H), 7.2-7.4 delta (m, 7H) 6.4 delta (d, 1H), 3.8 delta (s,3H), 3.3 delta (s,3H), 3.1 delta (1H), 2.8 delta (q, 1H), 2.6 delta (m, 3H), 1.7 delta (s,2H), 1.3-1.4 delta (m7H), 0.9 delta (t, 3H). 13 C NMR (75 MHz, CDCl3 with TMS): 12.1 delta, 23.9 delta, 25.3 delta, 26.2 delta, 27.3 delta, 37.5 delta, 38.2 delta, 49.8 delta, 50.7 delta, 55.5 delta, 59.7 delta, 75.6 delta, 75.6 delta, 101.8 delta, 119.1 delta, 121.8 delta, 126.3 delta, 126.7 delta, 127.3 delta, 129.1 delta, 131.7, delta143.1 delta, 144.7 delta, 144.9 delta, 147.5 delta, 152.1 delta, 154.8 delta, 157.7 delta. |
65% | With sodium hydroxide; triethylamine; In dichloromethane; | EXAMPLE 23 Synthesis of Methylphenylcarbamoyl <strong>[1435-55-8]di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong></strong> (MPC-DHQD) Di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong> (1.4 g, 4.3 mmol, 1 eq) was dissolved in 15 ml of CH2 Cl2 under nitrogen atmosphere in a 3-necked 100 ml round bottom flask. At room temperature, 2 ml of triethylamine (14.4 mmol, 3.3 eq) was added to the solution and stirred for 30 minutes. N-methyl-N-phenylcarbamoyl chloride (1.6 g, 9.4 mmol, 2.2 eq) was dissolved in 6 ml CH2 Cl2 and added to the reaction mixture dropwise via an addition funnel. The reaction mixture was stirred under N2 for three days before reaching reaction completion. 50 ml of 2N NaOH were added, and the phases were separated. The CH2 Cl2 layer was saved and the aqueous phase was extracted with 50 ml of CH2 Cl2. The CH2 Cl2 phases were combined and dried over MgSO4 before being concentrated down to afford a gummy pink material. Purification via flash chromatography (silica gel, 95.5 EtOAc/Et3 N, v/v) afforded a yellow material which was then crystallized from CH3 CN to obtain white starlike crystals (1.27 g, 65% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With sodium hydride In tetrahydrofuran; mineral oil at 25℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; isopropyl alcohol; at 70℃; for 7h;Inert atmosphere; | A slurry of <strong>[1435-55-8]quinidine</strong> (11, 8.1 g, 23.7 mmol, containing -14% <strong>[1435-55-8]di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong></strong>) and 2-bromo-5-methoxybenzylbromide (12, 16.59 g, 59.3 mmol) in EPA (4.0 ml) and DMF (28.4 mL) was degassed by vacuum and flushed with N2 , then heated to 70 C for 7 h. The reaction mixture was cooled to 22 C, this reaction solution was charged to AcOEt (320 ml) at 22 C over 10 min while stirring. The resulting slurry was aged at 22 C for 1 to 2 h, filtered, rinsed with AcOEt (2 x 24 ml), then hexane (2 x 24 ml). The solid was dried under vacuum to give powder as a mixture of bis-salts (bis-<strong>[1435-55-8]quinidine</strong> salt 10 and bis-<strong>[1435-55-8]di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong></strong> salt). (Total 19.7 g, 94% yield). The authentic sample of 10 was purified by SFC (IC column, 20 x 250 mm, 60% MeOH/C02, 50 mL/min, 100 bar, 35C, 220 nm, sample concentration: 133 mg/mL in MeOH; desired peak: 3 to 4.5 min). lH NMR (CDC13, 500 MHz): 8 9.34 (d, J = 6.1 Hz, 1H), 8.46 (d, J = 6.1 Hz, 1H), 8.38 (d, J= 9.7 Hz, 1H), 8.0 (dd, J= 9.7, 2.1 Hz, 1H), 7.86 (s, 1H), 7.79 (d, J = 8.9 Hz, 1H), 7.74 (d, J = 8.9 Hz, 1H), 7.60 (d, J= 2.5 Hz, 1H), 7.42 (d, J = 2.3 Hz, 1H), 7.17 (dd, J= 8.8, 2.8 Hz, 1H), 7.03 (dd, J= 8.8, 2.7 Hz, 1H), 6.93 (s, 1H), 6.50 (d, J= 2.4 Hz, 1 H), 6.06 (m, 1H), 5.24 (m, 3H), 4.95 (d, J= 12.9 Hz, 1H), 4.37 (m, 1H), 4.23 (m, 4H),4.12 (m, 1H), 3.88 (s, 3H), 3.69 (s, 3H), 3.54 (m, IH), 3.32 (s, 2H), 3.23 (m, IH), 2.71 (m, IH), 2.51 (s, 2H), 2.33 (m, IH), 1.94 (br, IH), 1.83 (br, 2H), 1.17 (br, IH); 13C NMR (DMSO-d6, 100 Hz): 6 159.45, 159.07, 158.67, 156.12, 146.01, 137.08, 134.68, 134.30, 133.21 , 132.98, 128.18, 128.03, 127.45, 122.13, 121.89, 121.22, 1 18.08, 1 17.5, 1 17.07, 1 16.73, 1 16.20, 1 15.81, 1 12.67, 105.09, 66.81, 65.51, 62.43, 56.75, 56.06, 55.91 , 55.52, 54.80, 36.84, 25.91, 23.10, 20.75. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | In tetrahydrofuran at 75℃; Inert atmosphere; | |
In acetone at 50 - 65℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; | Weigh <strong>[1435-55-8]di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong></strong> (0.5 mmol), A carboxylic acid (0.6 mmol) represented by Formula IIa, DCC (0.6 mmol) and DMAP (0.1 mmol) in a 50 mL flask, The dichloromethane (10 mL) which has been dried for the use of calcium hydride was added to the above reaction solution, and the reaction was performed at room temperature for 24-96 h. TLC tracking detected that the raw material reaction was complete. Urea was removed by filtration, and the filtrate obtained by filtration was diluted with dichloromethane (40 mL). The diluted solution was washed with 0.1 mol / L hydrochloric acid (25 mL), saturated sodium bicarbonate (25 mL), and saturated brine (25 mL) in that order, and then the washed dichloromethane solution was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a solid, which was then separated by silica gel column chromatography to obtain a <strong>[1435-55-8]di<strong>[1435-55-8]hydro<strong>[1435-55-8]quinidine</strong></strong></strong> compound represented by Formula Ia. The eluent of silica gel column chromatography is a mixed solvent of ethyl acetate and petroleum ether, wherein the volume ratio of ethyl acetate to petroleum ether is 4: 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | Stage #1: dihydroquinidine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 25℃; for 3h; Inert atmosphere; Stage #2: benzyl chloride In N,N-dimethyl-formamide; mineral oil at 25℃; Inert atmosphere; | |
Stage #1: dihydroquinidine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; Inert atmosphere; Stage #2: benzyl chloride In N,N-dimethyl-formamide; mineral oil at 20℃; for 17.17h; Inert atmosphere; | Synthesis of dihydroquinidine benzyl ether (DHQD-Bn) Adapted from the reported syntheses of similar cinchona alkaloid benzyl ethers [5,6,8,10,11], DHQD(2.0 g, 6.2 mmol) was dissolved in dry DMF (20 mL) followed by addition of NaH (0.68 g, 60%dispersion in mineral oil, 17 mmol). The resulting mixture was stirred at room temperature under inertatmosphere for 2 h. Then, benzyl chloride (0.75 mL, 0.83 g, 6.5 mmol) was added dropwise over thecourse of 10 minutes. The resulting mixture was stirred at room temperature under inert atmosphere for17 h. Upon completion of this time, brine (50 mL) was added carefully and the resulting mixture wasextracted with EtOAc (40 mL). The organic phase was washed with water (3 × 100 mL), dried overNa2SO4, and concentrated under reduced pressure. Column chromatography with ethyl acetate/methanol99:1 provided DHQD-Bn as light yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With sodium hydride In dimethyl sulfoxide; mineral oil |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | Stage #1: dihydroquinidine With sodium hydride In dimethyl sulfoxide; mineral oil at 25℃; for 0.5h; Inert atmosphere; Stage #2: With pyridine; copper (I) iodide In dimethyl sulfoxide; mineral oil for 0.5h; Inert atmosphere; Stage #3: 1-Iodonaphthalene In dimethyl sulfoxide; mineral oil at 113℃; for 70h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56 % | With potassium hydride In tetrahydrofuran at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10 % | With potassium hydride In tetrahydrofuran at 20℃; Inert atmosphere; |
Tags: 1435-55-8 synthesis path| 1435-55-8 SDS| 1435-55-8 COA| 1435-55-8 purity| 1435-55-8 application| 1435-55-8 NMR| 1435-55-8 COA| 1435-55-8 structure
A494936[ 1476-98-8 ]
(S)-((1S,2R,4S,5R)-5-Ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methanol hydrochloride
Reason: Free-salt
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Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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