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CAS No. : | 6725-45-7 | MDL No. : | MFCD00833397 |
Formula : | C10H10Cl2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QAEBVJIVEPSFRK-UHFFFAOYSA-N |
M.W : | 233.09 | Pubchem ID : | 2737422 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | 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 toluene-4-sulfonic acid for 2h; Reflux; | |
85% | With sulfuric acid for 12h; Reflux; | |
With sulfuric acid In benzene |
Stage #1: ethanol; 3,4-dichlorophenyl acetic acid With hydrogenchloride for 2h; Reflux; Stage #2: With ammonium hydroxide In water | 1 Example 1Preparation of l(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane[00129] As described in U.S. Patent No. 4,23 1 ,935, a solution of 59.5 g of 3,4- dichlorophenylacetic acid in 500 ml of absolute ethanol is saturated with anhydrous hydrogen chloride and then heated at reflux for 2 hours. The mixture is concentrated under reduced pressure to 200 ml, diluted with 200 ml of water and neutralized with concentrated ammonium hydroxide. This aqueous mixture is extracted 3 times with chloroform. Concentration and decolorization of the chloroform extracts gives ethyl 3,4- dichlorophenylacetate as a yellow oil.[00130] In a three-necked flask fitted with a Nichrome stirrer and a reflux condenser is placed 7.0 g of ethyl 3,4-dichlorophenylacetate, 5.9 g of N- bromosuccinimide, 0.1 g of benzoyl peroxide and 150 ml of carbon tetrachloride. The reaction mixture is heated at reflux for 18 hours, cooled and filtered. The carbon tetrachloride filtrate is concentrated under reduced pressure to give a deep orange liquid. Vacuum disti llation at 1 15°-120° C. (0.5 mm) gives ethyl a-bromo-3,4- dichlorophenylacetate as a pale yellow liquid.[00131] This product is converted to diethyl cis-l -(3,4-dichlorophenyl)- l ,2- cyclopropanedicarboxylate by the method of L. L. McCoy, J.A.C.S., 80, 6568 (1958).[00132] A mixture of 150 g of this diester and 66 g of 85% KOH in 500 ml of water and 500 ml of ethanol is refluxed for 6 hours and then chilled in ice. The oily material is extracted into ether and the aqueous layer is made acidic with 100 ml of 12 N hydrochloric acid. The oily lower layer crystallizes slowly to give a colorless crystalline cake. This is recrystallized from a mixture of ethanol and ethyl acetate to give colorless crystals of l -(3,4-dichlorophenyl)-l ,2-cyclopropanedicarboxylic acid.[00133] A mixture of 30.3 g of this diacid and 12.6 g of urea in one liter of xylene is refluxed for 6 hours. The solvent is stripped under reduced pressure and the crystalline residue is slurried with water. The colorless crystals are collected by filtration, washed with water and air dried to give l -(3,4-dichlorophenyl)-l ,2-cyclopropanedicarboximide.[00134] To 40 ml of 1 molar borane-tetrahydrofuran is added with stirring under nitrogen at 0° C. a solution of 2.56 g of this imide in 50 ml of tetrahydrofuran during 15 minutes. The solution is warmed in a steam bath for 1 hour and is then cooled in ice, and then 20 ml of 6 N hydrochloric acid is added, and the tetrahydrofuran is removed under reduced pressure. The residue is made basic with 75 ml of 5 N sodium hydroxide and this is extracted with ether. The extract is dried over magnesium sulfate, filtered, and the filtrate is saturated with hydrogen chloride. The precipitated crystals are collected by filtration and are recrystallized from isopropyl alcohol to give 1 .70 g of 1 -(3,4- dichlorophenyl)-3-azabicyclo[3.1.0]hexane hydrochloride as colorless crystals, m.p. 180°- 181° C. | |
With sulfuric acid Reflux; | ||
With hydrogenchloride for 2h; Reflux; | I As described in U.S. Pat. No. 4,231,935, a solution of 59.5 g of 3,4-dichlorophenylacetic acid in 500 ml of absolute ethanol is saturated with anhydrous hydrogen chloride and then heated at reflux for 2 hours. The mixture is concentrated under reduced pressure to 200 ml, diluted with 200 ml of water and neutralized with concentrated ammonium hydroxide. This aqueous mixture is extracted 3 times with chloroform. Concentration and decolorization of the chloroform extracts gives ethyl 3,4-dichlorophenylacetate as a yellow oil. | |
With sulfuric acid | ||
With sulfuric acid for 2h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 125℃; | ||
at 125℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45.5% | With sodium amide In diethyl ether at 5 - 10℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With N-Bromosuccinimide; hydrogen bromide In tetrachloromethane Heating; | |
With N-Bromosuccinimide In tetrachloromethane for 5h; Irradiation; | ||
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 18h; Reflux; | 1 Example 1Preparation of l(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane[00129] As described in U.S. Patent No. 4,23 1 ,935, a solution of 59.5 g of 3,4- dichlorophenylacetic acid in 500 ml of absolute ethanol is saturated with anhydrous hydrogen chloride and then heated at reflux for 2 hours. The mixture is concentrated under reduced pressure to 200 ml, diluted with 200 ml of water and neutralized with concentrated ammonium hydroxide. This aqueous mixture is extracted 3 times with chloroform. Concentration and decolorization of the chloroform extracts gives ethyl 3,4- dichlorophenylacetate as a yellow oil.[00130] In a three-necked flask fitted with a Nichrome stirrer and a reflux condenser is placed 7.0 g of ethyl 3,4-dichlorophenylacetate, 5.9 g of N- bromosuccinimide, 0.1 g of benzoyl peroxide and 150 ml of carbon tetrachloride. The reaction mixture is heated at reflux for 18 hours, cooled and filtered. The carbon tetrachloride filtrate is concentrated under reduced pressure to give a deep orange liquid. Vacuum disti llation at 1 15°-120° C. (0.5 mm) gives ethyl a-bromo-3,4- dichlorophenylacetate as a pale yellow liquid.[00131] This product is converted to diethyl cis-l -(3,4-dichlorophenyl)- l ,2- cyclopropanedicarboxylate by the method of L. L. McCoy, J.A.C.S., 80, 6568 (1958).[00132] A mixture of 150 g of this diester and 66 g of 85% KOH in 500 ml of water and 500 ml of ethanol is refluxed for 6 hours and then chilled in ice. The oily material is extracted into ether and the aqueous layer is made acidic with 100 ml of 12 N hydrochloric acid. The oily lower layer crystallizes slowly to give a colorless crystalline cake. This is recrystallized from a mixture of ethanol and ethyl acetate to give colorless crystals of l -(3,4-dichlorophenyl)-l ,2-cyclopropanedicarboxylic acid.[00133] A mixture of 30.3 g of this diacid and 12.6 g of urea in one liter of xylene is refluxed for 6 hours. The solvent is stripped under reduced pressure and the crystalline residue is slurried with water. The colorless crystals are collected by filtration, washed with water and air dried to give l -(3,4-dichlorophenyl)-l ,2-cyclopropanedicarboximide.[00134] To 40 ml of 1 molar borane-tetrahydrofuran is added with stirring under nitrogen at 0° C. a solution of 2.56 g of this imide in 50 ml of tetrahydrofuran during 15 minutes. The solution is warmed in a steam bath for 1 hour and is then cooled in ice, and then 20 ml of 6 N hydrochloric acid is added, and the tetrahydrofuran is removed under reduced pressure. The residue is made basic with 75 ml of 5 N sodium hydroxide and this is extracted with ether. The extract is dried over magnesium sulfate, filtered, and the filtrate is saturated with hydrogen chloride. The precipitated crystals are collected by filtration and are recrystallized from isopropyl alcohol to give 1 .70 g of 1 -(3,4- dichlorophenyl)-3-azabicyclo[3.1.0]hexane hydrochloride as colorless crystals, m.p. 180°- 181° C. |
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 18h; Reflux; | I In a three-necked flask fitted with a Nichrome stirrer and a reflux condenser is placed 7.0 g of ethyl 3,4-dichlorophenylacetate, 5.9 g of N-bromosuccinimide, 0.1 g of benzoyl peroxide and 150 ml of carbon tetrachloride. The reaction mixture is heated at reflux for 18 hours, cooled and filtered. The carbon tetrachloride filtrate is concentrated under reduced pressure to give a deep orange liquid. Vacuum distillation at 115°-120° C. (0.5 mm) gives ethyl α-bromo-3,4-dichlorophenylacetate as a pale yellow liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 25℃; for 24h; | |
56% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 13h; | |
With 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; |
With 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 15h; | ||
With 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; for 15h; | ||
With 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; | ||
With 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; | ||
With 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 79% 2: 6% | With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - 20℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 72% 2: 7% | With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - 20℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Stage #1: pyridine-4-carbonitrile; ethyl 3,4-dichlorophenylacetate With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide; <i>tert</i>-butyl alcohol at 20℃; for 1.5h; Stage #2: methyl thioisocyanate In N,N-dimethyl-formamide; <i>tert</i>-butyl alcohol at 20℃; for 1h; Stage #3: methyl iodide In N,N-dimethyl-formamide; <i>tert</i>-butyl alcohol at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 56 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 13 h / 20 °C 2: 98 percent / pentacarbonyl(η2-cis-cyclooctene)chromium(0) / CH2Cl2 / 8 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether / 0.25 h / Heating 2: NEt3 / CH2Cl2 / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: LiAlH4 / diethyl ether / 0.25 h / Heating 2: NEt3 / CH2Cl2 / 1 h / 0 °C 3: ethanol / 1 h / Heating 4: 1-hydroxybenzotriazole, NEt3, dicyclohexylcarbodiimide / dimethylformamide / 48 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: LiAlH4 / diethyl ether / 0.25 h / Heating 2: NEt3 / CH2Cl2 / 1 h / 0 °C 3: ethanol / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: LiAlH4 / diethyl ether / 0.25 h / Heating 2: NEt3 / CH2Cl2 / 1 h / 0 °C 3: ethanol / 1 h / Heating 4: 1-hydroxybenzotriazole, NEt3, dicyclohexylcarbodiimide / dimethylformamide / 48 h / Ambient temperature 5: 2 M HCl, HOAc / 1 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: LiAlH4 / diethyl ether / 0.25 h / Heating 2: NEt3 / CH2Cl2 / 1 h / 0 °C 3: ethanol / 1 h / Heating 4: 1-hydroxybenzotriazole, NEt3, dicyclohexylcarbodiimide / dimethylformamide / 48 h / Ambient temperature 5: 2 M HCl, HOAc / 1 h / Ambient temperature 6: 1-hydroxybenzotriazole, N-methylmorpholine, dicyclohexylcarbodiimide / dimethylformamide / 48 h / 4 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: LiAlH4 / diethyl ether / 0.25 h / Heating 2: NEt3 / CH2Cl2 / 1 h / 0 °C 3: ethanol / 1 h / Heating 4: 1-hydroxybenzotriazole, NEt3, dicyclohexylcarbodiimide / dimethylformamide / 48 h / Ambient temperature 5: 2 M HCl, HOAc / 1 h / Ambient temperature 6: 1-hydroxybenzotriazole, N-methylmorpholine, dicyclohexylcarbodiimide / dimethylformamide / 48 h / 4 °C 7: anisole, 2 M HCl / 0.5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: LiAlH4 / diethyl ether / 0.25 h / Heating 2: NEt3 / CH2Cl2 / 1 h / 0 °C 3: ethanol / 1 h / Heating 4: 1-hydroxybenzotriazole, NEt3, dicyclohexylcarbodiimide / dimethylformamide / 48 h / Ambient temperature 5: 2 M HCl, HOAc / 1 h / Ambient temperature 6: 1-hydroxybenzotriazole, N-methylmorpholine, dicyclohexylcarbodiimide / dimethylformamide / 48 h / 4 °C 7: anisole, 2 M HCl / 0.5 h / Ambient temperature 8: 77 percent / NEt3 / dimethylformamide; ethanol / 7.5 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 80 percent / NBS, 48percent aq. HBr / CCl4 / Heating 2: 29 percent / NaOEt / diethyl ether / 24 h / Ambient temperature 3: 40 percent / KOH / ethanol; H2O / 6 h / Heating 4: 84 percent / urea / xylene / Heating 5: 65 percent / BH3 / tetrahydrofuran / 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 80 percent / NBS, 48percent aq. HBr / CCl4 / Heating 2: 29 percent / NaOEt / diethyl ether / 24 h / Ambient temperature 3: 40 percent / KOH / ethanol; H2O / 6 h / Heating 4: 84 percent / urea / xylene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 80 percent / NBS, 48percent aq. HBr / CCl4 / Heating 2: 29 percent / NaOEt / diethyl ether / 24 h / Ambient temperature 3: 40 percent / KOH / ethanol; H2O / 6 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 80 percent / NBS, 48percent aq. HBr / CCl4 / Heating 2: 29 percent / NaOEt / diethyl ether / 24 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 45.5 percent / NaNH2 / diethyl ether / 3 h / 5 - 10 °C 2: 60 percent / H2, AcOH / 5percent Pt/C / 1.5 h / 120 °C / 105008 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 45.5 percent / NaNH2 / diethyl ether / 3 h / 5 - 10 °C 2: H2, AcOH / 5percent Pt/C / 1.5 h / 120 °C / 105008 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: NBS / CCl4 / 5 h / Irradiation 2: dimethylformamide / Ambient temperature; electrolysis |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: NaH / benzene 2: ClO3F, NaH / dimethylformamide 3: KOH, EtOH 4: (heating) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: NaH / benzene 2: ClO3F, NaH / dimethylformamide 3: KOH, EtOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: NaH / benzene 2: ClO3F, NaH / dimethylformamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: NaH / benzene 2: ClO3F, NaH / dimethylformamide 3: KOH, EtOH 4: (heating) 5: HCl |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In ethanol | 7 Synthesis of Ethyl 3,4-Dichlorophenylacetate EXAMPLE 7 Synthesis of Ethyl 3,4-Dichlorophenylacetate 90.05 g of 3,4-dichlorophenylacetic acid was dissolved in 150 ml of ethanol, and the solution was treated according to the procedure of Example 5 to obtain 101.30 g (90.0% yield) of the title substance. 1H-NMR (600 MHz, TMS, CDCl3); 1.24 (3H, t, J=6.0 Hz), 3.52 (2H, s), 4.08 (2H, q, J=6.0 Hz), 7.10 (1H, dd, J=2.0, 8.0 Hz), 7.32 (1H, d, J=8.0 Hz), 7.33 (1H, d, J=2.0 Hz), b. p. 136-138° C./7 mmHg. |
With sulfuric acid In ethanol | 1.a 3-[1-(3,4-Dichlorophenyl)-3-(4-hydroxy-4-phenylpiperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochloride a. Ethyl 3,4-dichlorophenylacetate. A solution of 3,4-dichlorophenylacetic acid (39 g) in ethanol (300 mL) was treated with concentrated sulfuric acid (15 mL) and refluxed for 16 hours. The reaction mixture was cooled to the room temperature, diluted with water and ether. The organic layer was washed (water and saturated sodium bicarbonate solution), dried and evaporated to afford the ester (44.27 g); MS: m/z=233(M+1); NMR: 1.2 (t,3, J=4), 3.76 (s,2), 4.09 (q,2, J=4), 7.28 (dd,1, J=5, 1) 7.57 (m,2). | |
In ethanol; water | 23 1-(3,4-Dichlorophenyl)-3-azabicyclo[3.1.0]hexane hydrochloride EXAMPLE 23 1-(3,4-Dichlorophenyl)-3-azabicyclo[3.1.0]hexane hydrochloride A solution of 59.5 g. of 3,4-dichlorophenylacetic acid in 500 ml. of absolute ethanol is saturated with anhydrous hydrogen chloride and then heated at reflux for 2 hours. The mixture is concentrated under reduced pressure to 200 ml., diluted with 200 ml. of water and neutralized with concentrated ammonium hydroxide. This aqueous mixture is extracted 3 times with chloroform. Concentration and decolorization of the chloroform extracts gives ethyl 3,4-dichlorophenylacetate as a yellow oil. |
In ethanol; water | 27 Preparation of 1-(3,4-Dichlorophenyl)-3-azabicyclo[3.1.0]hexane EXAMPLE 27 Preparation of 1-(3,4-Dichlorophenyl)-3-azabicyclo[3.1.0]hexane A solution of 59.5 g of 3,4-dichlorophenylacetic acid in 500 ml of absolute ethanol is saturated with anhydrous hydrogen chloride and then heated at reflux for 2 hours. The mixture is concentrated under reduced pressure to 200 ml, diluted with 200 ml of water and neutralized with concentrated ammonium hydroxide. This aqueous mixture is extracted 3 times with chloroform. Concentration and decolorization of the chloroform extracts gives ethyl 3,4-dichlorophenylacetate as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; dimethyl sulfoxide; sodium sulfate In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; hexane; water | 8 Synthesis of 3-(3,4-Dichlorophenyl)-3-ethoxycarbonylpropionic Acid EXAMPLE 8 Synthesis of 3-(3,4-Dichlorophenyl)-3-ethoxycarbonylpropionic Acid 16.50 g of sodium hydride with 64% purity and 350 ml of dry dimethyl sulfoxide were supplied to a well dried 1-litre 4-necked flask. Then 101.30 g of ethyl 3,4-dichlorophenylacetate obtained in Example 6 was added dropwise, the solution being stirred at room temperature even after the end of the dropwise addition. Thereafter, 48.61 g of sodium chloroacetate was added and the solution was further stirred at room temperature. At this point, the reaction solution changed from a yellow to a red suspension. The reaction solution was stirred overnight at room temperature, then poured into a mixture of 500 ml of 1N hydrochloric acid and 300 ml of ice water, and stirred vigorously. The reaction mixture was extracted with 800 ml of ether and the organic layer was washed with 500 ml of water (three times) and 500 ml of a saturated saline solution (once). This organic layer was then dried over approximately 50 g of anhydrous sodium sulfate, concentrated to approximately 50 ml solvent and crystallized by treating it with approximately 300 ml of an ether/hexane mixed solvent. The precipitated crystals were filtered out and dried to give 106.07 g of primary crystals of the title substance. Meanwhile, the filtrate was concentrated to produce an oily substance, and it was crystallized by adding 20 ml of ether and 60 ml of hexane. Further, after additional supply of hexane, the precipitated crystals were filtered out and dried to obtain 3.09 g of the secondary crystals (109.16 g when combined with the primary crystals, yield 84.0%) of the title substance. 1H-NMR (200 MHzFT, TMS, CDCl3); 1.21 (3H, t, J=7.2 Hz), 2.70 (1H, dd, J=5.7, 17.4 Hz), 3.21 (1H, dd, J=9.6, 17.4 Hz), 4.00 (1H, dd, J=5.7, 9.6 Hz), 4.15 (2H, q, J=7.0 Hz), 7.13 (1H, dd, J=2.1, 8.4 Hz), 7.39 (1H, s), 7.41 (1H, d, J=8.4 Hz). MS(FAB, m-NBA); m/z-→291 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium chloride; ammonium chloride; sodium hydrogencarbonate In tetrahydrofuran | 1.b 3-[1-(3,4-Dichlorophenyl)-3-(4-hydroxy-4-phenylpiperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochloride b. 2-(3,4-Dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butyric acid ethyl ester. A solution of ethyl 3,4-dichlorophenylacetate (23.3 g) in tetrahydrofuran (50 mL) was treated with sodium hydride (4.0 g of 60% dispersion in oil) and the suspension was stirred at room temperature for 1.5 hours. The reaction mixture was cooled to 0° C. and treated with a solution of 1-bromo-2-(tetrahydropyran-2-yloxy)ethane (20.9 g) in tetrahydrofuran (50 mL). Upon stirring at ambient temperature for 16 hours, the reaction mixture was treated with saturated ammonium chloride solution, ether, sodium chloride solution and sodium bicarbonate solution. The organic layer was separated and the aqueous layer was extracted with ether. The combined organic extracts were washed with sodium bicarbonate solution, dried and evaporated to obtain an oil. Chromatography, eluding with dichloromethane, afforded the ether (5.87 g); MS: m/z=277(M-84); NMR: 1.14 (t,3, J=7), 1.94 (m,1), 2.27 (m,1), 3.62 (m,2), 3.80 (m,1), 4.08 (m,2), 4.48 (m,1), 7.31 (m,1), 7.59 (m,2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium chloride In tetrahydrofuran | 2.a (3R*)-3-[(1R*)-1-(3,4-Dichlorophenyl)-3-(4-hydroxy-4-phenylpiperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochloride a. 2-(3,4-Dichlorophenyl)pent-4-enoic acid ethyl ester. To a suspension of sodium hydride (4.0 g of 60% dispersion in oil) in tetrahydrofuran (25 mL) at 0° C. was added a solution of the ethyl 3,4-dichlorophenylacetate (23.3 g) and the suspension was stirred at room temperature for 2 hours. The reaction mixture was cooled to -15° C. and treated with allyl bromide (12.1 g). Upon stirring at ambient temperature for 16 hours, the reaction mixture was quenched with saturated ammonium chloride solution and diluted with ether. The aqueous layer was extracted with ether and the combined organic layers were washed with brine. Drying and evaporation of the organic layer gave the alkene (20.2 g); MS: m/z=273(M+1); NMR (CDCl3): 1.19 (t,3, J=7), 2.7 (m,2), 3.57 (m,1), 4.11 (m,2), 5.0 (m,2), 5.7 (m,1), 7.15-7.42 (m,2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | Stage #1: ethyl 3,4-dichlorophenylacetate With sodium hydride; oxalic acid diethyl ester In ethanol; m-xylene at 0 - 20℃; for 14h; Stage #2: formaldehyd In ethanol; water; m-xylene at 20℃; for 1h; Stage #3: With potassium carbonate In ethanol; water; m-xylene at 20℃; for 1h; | 2.1 (Step 1) To a solution of sodium hydride (60% in oil, 6.56 g) in m-xylene (100 mL) was slowly added ethanol (15.7 mL) at 0° C. and then diethyl oxalate (32.0 g) was added. Furthermore, a solution of ethyl 3,4-dichlorophenylacetate (51.0 g) in m-xylene (30 mL) was added at 0° C., and the mixture was stirred at room temperature for 14 hr. To the reaction mixture was added 37% aqueous formalin solution (140 mL) at room temperature, and the mixture was stirred at room temperature for 1 hr. Furthermore, potassium carbonate (115 g) was added at room temperature, and the mixture was stirred at room temperature for 1 hr. The insoluble material was filtered off, and the filtrate was partitioned between ethyl acetate (500 mL) and water (500 mL). The organic layer was separated, washed with brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent; 5% ethyl acetate/hexane) to give crude ethyl 2-(3,4-dichlorophenyl)acrylate (38.1 g, 44%) as a colorless oil.1H-NMR (CDCl3): δ 1.34 (3H, t, J=7.2 Hz), 4.29 (2H, q, J=7.2 Hz), 5.92 (1H, d, J=1.0 Hz), 6.12 (1H, d, J=1.0 Hz), 7.26 (1H, dd, J=8.4, 2.2 Hz), 7.43 (1H, d, J=8.4 Hz), 7.54 (1H, d, J=2.2 Hz) |
With tetra-(n-butyl)ammonium iodide; potassium carbonate In toluene at 60℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | Stage #1: ethyl 3,4-dichlorophenylacetate With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.75h; Inert atmosphere; Stage #2: Isobutyl iodide In tetrahydrofuran at -78 - 25℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With ammonium chloride; sodium nitrite In water; toluene at 100℃; for 24h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium hydride In tetrahydrofuran; mineral oil for 2h; Reflux; | 5 5.5 Diethyl(3,4-dichlorophenyl)propanedioate (26a) To a solution of ethyl 2-(3,4-dichlorophenyl)acetate (5.0g, 21mmol) in THF (60mL) were added NaH (60% in oil, 1.7g, 43mmol) and diethyl carbonate (13mL, 110mmol) at room temperature. After being refluxed for 2h, the reaction mixture was quenched with satd NH4Cl aq and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give 26a (6.6g, 100%) as a pale yellow oil. 1H NMR (CDCl3) δ: 1.25-1.33 (6H, m), 4.11-4.28 (4H, m), 4.54 (1H, s), 7.24-7.27 (1H, m), 7.43 (1H, d, J=8.1Hz), 7.51 (1H, d, J=2.4Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C 2.1: copper(l) iodide; cesium fluoride / 1-methyl-pyrrolidin-2-one / 0.17 h / 20 °C / Glovebox; Schlenk technique 2.2: 11 h / 40 °C / Glovebox; Schlenk technique; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; tetra-(n-butyl)ammonium iodide / toluene / 60 °C / Inert atmosphere 2: lithium hydroxide / tetrahydrofuran; water / 60 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: potassium hexamethylsilazane / tetrahydrofuran / 1.25 h / -78 - 20 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: lithium hydroxide / tetrahydrofuran; water / 6 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; tetra-(n-butyl)ammonium iodide / toluene / 60 °C / Inert atmosphere 2: lithium hydroxide / tetrahydrofuran; water / 60 °C / Inert atmosphere 3: thionyl chloride / dichloromethane / 55 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate; tetra-(n-butyl)ammonium iodide / toluene / 60 °C / Inert atmosphere 2: lithium hydroxide / tetrahydrofuran; water / 60 °C / Inert atmosphere 3: thionyl chloride / dichloromethane / 55 °C / Inert atmosphere 4: triethylamine / dichloromethane / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium carbonate; tetra-(n-butyl)ammonium iodide / toluene / 60 °C / Inert atmosphere 2: lithium hydroxide / tetrahydrofuran; water / 60 °C / Inert atmosphere 3: thionyl chloride / dichloromethane / 55 °C / Inert atmosphere 4: triethylamine / dichloromethane / 20 °C / Inert atmosphere 5: palladium diacetate; p-benzoquinone; phosphoric acid dibenzyl ester / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C 2: water; C18BF15*(x)H2O / 3 h / 40 °C / Sealed tube; Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C / Inert atmosphere; Schlenk technique 2: tris(pentafluorophenyl)borate; trimethylsilylazide / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere; Schlenk technique; Molecular sieve |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: Methyltriphenylphosphonium bromide With potassium hexamethylsilazane In tetrahydrofuran at -78 - 20℃; for 1.25h; Inert atmosphere; Stage #2: ethyl 3,4-dichlorophenylacetate In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 °C 2: lithium hydroxide / tetrahydrofuran; water / 20 °C 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 °C 2: lithium hydroxide / tetrahydrofuran; water / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 °C 2: lithium hydroxide / tetrahydrofuran; water / 20 °C 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 °C 2: lithium hydroxide / tetrahydrofuran; water / 20 °C 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 2h; |
Tags: 6725-45-7 synthesis path| 6725-45-7 SDS| 6725-45-7 COA| 6725-45-7 purity| 6725-45-7 application| 6725-45-7 NMR| 6725-45-7 COA| 6725-45-7 structure
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Code | Phrase |
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Code | Phrase |
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P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
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P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
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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 | |
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P401 | |
P402 | Store in a dry place. |
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Disposal | |
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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 |
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H223 | Flammable aerosol |
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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 |
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H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
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Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
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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 |
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H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
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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 |
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