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CAS No. : | 628-89-7 | MDL No. : | MFCD00002870 |
Formula : | C4H9ClO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LECMBPWEOVZHKN-UHFFFAOYSA-N |
M.W : | 124.57 | Pubchem ID : | 12361 |
Synonyms : |
|
Num. heavy atoms : | 7 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 28.38 |
TPSA : | 29.46 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.05 cm/s |
Log Po/w (iLOGP) : | 1.67 |
Log Po/w (XLOGP3) : | 0.02 |
Log Po/w (WLOGP) : | 0.23 |
Log Po/w (MLOGP) : | 0.23 |
Log Po/w (SILICOS-IT) : | 0.79 |
Consensus Log Po/w : | 0.59 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.36 |
Solubility : | 54.3 mg/ml ; 0.436 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.19 |
Solubility : | 80.3 mg/ml ; 0.645 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.24 |
Solubility : | 7.22 mg/ml ; 0.0579 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.5 |
Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | 3334 |
Hazard Statements: | H315-H318-H335 | Packing Group: | Ⅲ |
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 |
---|---|---|
95.1% | With piperazine dihydrochloride In ethanol for 10 h; Reflux; Large scale | Add 150 kg of 95percent ethanol to the PM-RC-15 reaction tank, stir and open the feed port. Add 200 kg of piperazine bis-salt, 100 kg of piperazine to the reaction tank, dissolve it by heating, add 110 kg of chlorinated diethylene glycol, TheReaction is completed, reduced to 15-20 , centrifugal recovery of piperazine bischloride, the filtrate adjusted to pH 11, filter out sodium chloride, the filtrate vacuum distillation to collect liquid temperature of 154-160 , the top temperature of 145-148 (Yield: 95.1percent) of 90 kg of N- [2- (2-hydroxyethoxy) ethyl] piperazine as a fraction (vacuum: 2 mmHg). |
70% | at 120 - 140℃; for 1 h; | 100 g (1.2 mol) of anhydrous piperazine and 240 g (1.5 mol) of piperazine dihydrochloride are heated to 120 degrees Celsius,150 g (1.2 mol) of 2-(2-chloroethoxy)ethanol are added dropwise, and heating and stirring are continued after the addition.The temperature was raised to 136-140 degrees Celsius and held for 1 hour. TLC showed that the reaction was complete and the heating was stopped.When the temperature drops to 80 degrees Celsius, add 500 ml of 95percent ethanol and cool in the refrigerator overnight.The piperazine dihydrochloride was recovered by filtration the next day. The filter cake was washed thoroughly with a small amount of ethanol, and the filtrate was combined.Add 20percent sodium hydroxide solution 200 grams alkalinization, filter out insoluble inorganic salts;After removing the solvent by concentration and distilling off under reduced pressure, collect fractions at 168-172 degrees Celsius/10 mmHg.145 g of 1-[2-(2-hydroxyethoxy)ethyl] is obtained as a colorless to light yellow transparent liquid.Piperazine, yield 70percent, content more than 98percent; there is unknown impurity content in the range of 0.5 to 1percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73.3% | at 45 - 55℃; for 2.5 h; | Cooling the material inside the three-necked flask to 45-50 , 0.7g of boron trifluoride diethyl etherate was added, followed by stirring under fed 46.2g (1.05mol) of ethylene oxide passed into 1.5-2h time, maintaining the reaction temperature for the in the 45-55 , ethylene oxide to control the access speed, temperature-controlled water bath can be used if necessary. Meanwhile, to complete the reaction, the ethylene oxide after the end of pass, and stirring was continued reaction 0.5h. After completion of the reaction, heating, vacuum distillation under reduced pressure, taking intermediate fraction (fraction a temperature of 115-123 deg.] C, vacuum degree of 10 mmHg) as a colorless transparent liquid. The intermediate fractions were collected vacuum distillation under a reduced pressure, taking intermediate fraction (fraction a temperature of 118-121 deg.] C, vacuum degree of 10 mmHg) as a colorless transparent liquid, 123.6 g, 97.7percent gas phase content, total 73.3percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19.3% | Stage #1: With sodium tungstate; trioctylmethylammonium sulfate; dihydrogen peroxide In water at 90℃; for 4 h; Stage #2: With hydrogenchloride In diethyl ether; water |
Ethyleneglycol mono 2-chloroethyl ether (10 g, 0.08 mol) is added to an aqueous 30percent hydrogen peroxide solution (22.8 g, 0.2 mol) and thereto are added sodium tungustate dihydrate (0.53 g, 1.6 mmol) and trioctylmethylammonium sulfate (0.75 g, 1.6 mmol). The mixture is stirred at 90°C for 4 hours. After adding aqueous sodium thiosulfate solution, the mixture is extracted with ethyl acetate (50 mL). The organic layers are combined, washed, dried and concentrated to give oily residue (9 g). The residue is diluted with diethyl ether, and the insoluble materials are removed by filtration. The filtrate is partitioned by adding aqueous sodium bicarbonate. The aqueous layer is washed with diethyl ether and acidified with dilute hydrochloric acid, followed by extraction with ethyl acetate. The organic layers are combined, dried, and concentrated to give 2-chloroethoxyacetic acid (2.14 g, crude, 19.3percent) as oily residue. IR: ν = 3410, 1727, 1123, 1044 cm-1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With triethylamine In dichloromethane at 0 - 20℃; for 3 h; | To a stirred solution of 2-(2-chloroethoxy)ethan-l-ol 133 (20.0 g, 160 mmol) in dry DCM (50 mL), Et3N (33.4 mL, 176 mmol) was added and stirred at room temperature for 10 min. The reaction mixture was cooled to 0 °C and treated with a solution of acetic anhydride (16.6 mL, 240 mmol) in DCM (50 mL) dropwise, then allowed to warm to room temperature and stirred for a further 3h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography using 40percent EtOAc/hexane to afford 134. Yield: 17.5 g, 88 percent; 1H NMR (400 MHz, DMSO-d6) δ 4.12 (t, J= 4.5 Hz, 2H), 3.75- 3.60 (m, 6H), 2.02 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With sulfuric acid In ethanol; water; isopropyl alcohol; acetone | PREPARATION 2 Ethyl 2-chloroethoxyacetate A solution of 30 g of 2-(2-chloroethoxy)ethanol in 300 ml of acetone was added dropwise to a mixture of 240 ml of Jones' reagent (prepared by dissolving 133.5 g of chromium trioxide by adding 115 ml of concentrated sulfuric acid and water, followed by adding further water to a total volume of 500 ml) and 1050 ml of acetone at -5°-0° C., and the mixture was stirred at the same temperature for 30 minutes. At the end of this time, 150 ml of isopropanol were added to the mixture, which was then stirred at room temperature for 1 hour. At the end of this time, it was filtered, and the filtrate was concentrated by evaporation under reduced pressure and adjusted to a pH value of 3 by adding aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate, and the solvent was evaporated from the extract, to give 24.9 g (yield 75percent) of 2-chloroethoxyacetic acid as a pale green oil. Gaseous hydrogen chloride was passed through a solution of 24.9 g of this acid in 250 ml of ethanol, and the mixture was heated under reflux for 3 hours. At the end of this time, it was concentrated by evaporation under reduced pressure. Distillation gave 29.2 g (yield 95percent) of the title compound as a colorless oil, boiling at 96° C./14 mmHg (1866 Pa). |
75% | With sulfuric acid In ethanol; water; isopropyl alcohol; acetone | PREPARATION 2 Ethyl 2-chloroethoxyacetate A solution of 30 g of 2-(2-chloroethoxy)ethanol in 300 ml of acetone was added dropwise to a mixture of 240 ml of Jones' reagent (prepared by dissolving 133.5 g of chromium trioxide by adding 115 ml of concentrated sulfuric acid and water, followed by adding further water to a total volume of 500 ml) and 1050 ml of acetone at -5° C.-0° C., and the mixture was stirred at the same temperature for 30 minutes. At the end of this time, 150 ml of isopropanol were added to the mixture, which was then stirred at room temperature for 1 hour. At the end of this time, it was filtered, and the filtrate was concentrated by evaporation under reduced pressure and adjusted to a pH value of 3 by adding aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate, and the solvent was evaporated from the extract, to give 24.9 g (yield 75percent) of 2-chloroethoxyacetic acid as a pale green oil. Gaseous hydrogen chloride was passed through a solution of 24.9 g of this acid in 250 ml of ethanol, and the mixture was heated under reflux for 3 hours. At the end of this time, it was concentrated by evaporation under reduced pressure. Distillation gave 29.2 g (yield 95percent) of the title compound as a colorless oil, boiling at 96° C./14 mmHg (1866 Pa). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Stage #1: With sodium carbonate; sodium iodide In toluene at 105℃; for 24 h; Heating / reflux Stage #2: With (2E)-but-2-enedioic acid In tolueneHeating / reflux |
Reagents: 11-piperazinyl dibenzo[b,f][1,4] thiazepine hydrochloride 16.5 gr (44 mmole) 2- (2-Chloroethoxy) ethanol 7.2 gr (58 mmole) Na2C03 28.5 gr (270 mmole) NaI 270 mg (0.18 mmole) TBAB 3 gr Toluene 82.5 mL Procedure: The reagents were charged to a round-bottomed flask equipped with a magnetic stirrer and a condenser with a calcium chloride drying tube. The flask and contents were heated in an oil bath at 105C under gentle reflux. After 24 hours, a Dean Stark trap was attached to the flask and the azeotropic mixture of water and toluene was distilled out. The product remaining in the flask was filtered-off. The precipitate (salts) was washed on the Buchner filter with small portions of toluene. The washings were combined with the filtrate and the precipitate was discarded. To the filtrate contained in a flask was added 2.6 gr (22 mmole) fumaric acid. The mixture was heated to boiling on a heating bath and then was removed from the heating bath and stirring of the contents of theflask was continued. The quetiapine hemifumarate crystallized out. The flask was cooled in an ice bath and the contents filtered. The collected solid was recrystallized from 150 mL ethanol. Yield 14.0 grams 72percent. |
72% | Stage #1: With sodium carbonate; sodium iodide In toluene at 107℃; for 40 h; Heating / reflux Stage #2: With (2E)-but-2-enedioic acid In toluene at 100℃; |
Reagents: 11-piperazinyl dibenzo[b,f][1,4] thiazepine hydrochloride 33 gr (86.9 mmole) 2-(2-chloroethoxy)ethanol 14.4 gr (115.6 mmole) Na2CO3 57 gr Nal 540 mg TBAB 6 gr Toluene 165 gr Procedure: The reagents were charged to a round-bottomed flask equipped with a magnetic stirrer and a condenser with a calcium chloride drying tube. The flask was heated on an oil bath at 107C under gentle reflux. After 40 hours, the flask and contents were cooled slightly and contents of the flask filtered. The collected precipitate was washed with small portions of toluene. The washings were combined with the filtrate and the precipitate was discarded. The filtrate was divided into 4 equal portions which were worked up in four different ways : A: The filtrate was extracted with water. To the organic phase was added 1.43 gr (11.5 mmole) fumaric acid. The mixture was heated in a boiling water bath, removed from the bath and continued to stir. Quetiapine hemifumarate crystallized out. The product was filtered and recrystallized from 80 mL ethanol. Yield 6.91 grams 72percent. C: To the filtrate was added 1.43 gr (11.5 mmole) fumaric acid. It was heated in a boiling water bath, removed from the bath and let to stir. The Quetiapine hemifumarate crystallized out. The product was filtered and recrystallized from 90 mL ethanol. Yield 7.12 grams (73.3percent). |
70.8% | Stage #1: With sodium carbonate; sodium iodide In butan-1-ol at 115 - 120℃; for 24 h; Heating / reflux Stage #2: With (2E)-but-2-enedioic acid In butan-1-olHeating / reflux |
Reagents: 11-piperazinyl dibenzo[b,f][1,4] thiazepine hydrochloride 5.5 gr (15 mmole) 2-(2-Chloroethoxy) ethanol 2.4 gr (19 mmole) Na2C03 9.5 gr (90 mmole) NaI 90 mg (0.6 mmole) n-Butanol 30 mL TBAB 1 gr Procedure: The reagents were charged to a round-bottomed flask equipped with a magnetic stirrer and a condenser with a calcium chloride drying tube. The flask was set in an oil bath at 115C-120C and the contents of the flask stirred under gentle reflux. After 24 hours the heating was discontinued. The mixture was cooled and filtered. The precipitate collected on the Buchner filter was washed 2 times with butanol. The washings were combined with the filtrate and the precipitate was discarded. The filtrate was charged to a reaction vessel and fumaric acid (870 mg, 7.5 mmole) was charged to the vessel. The mixture was heated on an oil bath to boiling. The vessel was removed from the oil bath and the contents allowed to cool, whereapon quetiapine hemifumarate crystallized out. The product hemifumarate was filtered and recrystallized from 60 mL n-butanol. Yield 4.7 grams (70. 8percent). |
65.5% | Stage #1: With sodium carbonate; sodium iodide In toluene at 107℃; for 40 h; Heating / reflux Stage #2: With (2E)-but-2-enedioic acid In ethanol; tolueneHeating / reflux |
Reagents: 11-piperazinyl dibenzo[b,f][1,4] thiazepine hydrochloride 33 gr (86.9 mmole) 2-(2-chloroethoxy)ethanol 14.4 gr (115.6 mmole) Na2CO3 57 gr Nal 540 mg TBAB 6 gr Toluene 165 gr Procedure: The reagents were charged to a round-bottomed flask equipped with a magnetic stirrer and a condenser with a calcium chloride drying tube. The flask was heated on an oil bath at 107C under gentle reflux. After 40 hours, the flask and contents were cooled slightly and contents of the flask filtered. The collected precipitate was washed with small portions of toluene. The washings were combined with the filtrate and the precipitate was discarded. The filtrate was divided into 4 equal portions which were worked up in four different ways: B: The filtrate was extracted with water. The organic phase was evaporated down to a small volume to which was added 1.43 gr (11.5 mmole) fumaric acid with 120 mL ethanol. The reactants were heated to boiling. The heating was stopped and the quetiapine hemifumarate crystallized out. The product were continued to stir, filtered and recrystallized from 70 mL ethanol. Yield 6.36 grams (65.5percent) D: The filtrate was concentrated down to a small volume. 1.433 gr (11.5 mmole) fumaric acid was added with 120 mL ethanol. The mixture was heated to boiling, and removed from the heating bath. The quetiapine hemifumarate crystallized out and was cooled, filtered and recrystallized from 70 mL ethanol. Yield 6.62 grams (68.1). |
60.4% | Stage #1: With sodium carbonate; sodium iodide In butan-1-ol at 115 - 120℃; for 24 h; Heating / reflux Stage #2: With (2E)-but-2-enedioic acid In butan-1-ol at 100℃; |
Reagents: 11-piperazinyl dibenzo[b,f][1,4] thiazepine hydrochloride 2.75 gr (7.5 mmole) 2-(2-chloroethoxy)ethanol 1.2 gr (9.6 mmole) Na2C03 4.75 gr (45 mmole) Nal 40-50 mg (ca. 0.3 mmole) n-butanol 15 ml TBAB 0.5 gr Procedure: The reagents were charged to a round-bottomed flask and heated to 115C-120C under gentle reflux conditions for 24 hours. The heating was discontinued and the solution was cooled. The resulting slurry was filtered. The precipitate was washed twice with small portions of butanol. The washing were combined with the filtrate and the precipitate discarded. Fumaric acid (0. 435 g, 3.75 mmole) was added to the filtrate, the mixture was heated on a boiling water bath. The flask was removed from the bath and quetiapine hemifumarate crystallized out. The precipitate was collected (isolated) by filtration and recrystallized from 28 mL ethanol, yielding 2.0 grams (60.4percent). |
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