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CAS No. : | 86506-70-9 | MDL No. : | MFCD13192149 |
Formula : | C12H11NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 217.22 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P301+P312 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
99% | With 3-chloro-benzenecarboperoxoic acid In chloroform at 20℃; for 18h; | i.b 2-(2-(oxiran-2-yl)ethyl)isoindoline- 1.3-dione 2-(But-3-en-1-yl)isoindoline-1.3-dione A1 (4.31 g, 21.4 mmol), chloroform (50 mL) and mCPBA (70-75%, 6.34 g, 26 mmol 70%) were stirred at room temperature. After 20 hours the mixture was diluted with 10% w/v aqueous sodium thiosulfate solution (100 mL) and stirred vigorously for five minutes. The mixture was diluted with saturated aqueous sodium bicarbonate (100 mL), the organic layer separated and the aqueous layer extracted with chloroform (2 x 100 mL). The pooled organic extracts were washed with saturated aqueous sodium bicarbonate (100 mL), brine (100 mL), dried over sodium sulfate and concentrated in vacuo to give the title compound as a white solid (4.60 g, 99% yield). LCMS-B: rt 3.43 min; m/z (positive ion) 218.1 [M+H]+ |
94% | With 3-chloro-benzenecarboperoxoic acid In chloroform at 20℃; for 18h; | |
80% | With 3-chloro-benzenecarboperoxoic acid In ethyl acetate at 80℃; for 1h; |
79% | With 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane 1.) RT, 18 h, 2.) reflux, 1h; | |
With 3-chloro-benzenecarboperoxoic acid | ||
With 3-chloro-benzenecarboperoxoic acid | ||
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 10h; | 5.2 To a mixture of 2-(but-3-en-1-yl)isoindoline-1,3-dione obtained in step 1 (0.65 g, 3.22 mmol) in dichloromethane (10 ml), was added m-chloroperoxybenzoic acid (1.11 g, 6.44 mmol) at 0° C. The resulting reaction mixture was stirred at room temperature for 10 hours. After the reaction complete, the reaction mixture thus obtained was filtered through a plug of Celite. The filtrate was washed with 1 N sodium hydroxide solution and brine. The organic phase thus separated was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (0.65 g). The compound was used for the next step without further purification.MH+ 218. | |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | In N,N-dimethyl-formamide at 20℃; for 20h; Inert atmosphere; | |
94% | In N,N-dimethyl-formamide at 100℃; for 0.333333h; Microwave irradiation; | 2-(2-(Oxirane-2-yl)ethyl)isoindoline-1,3-dione (6b) To a suspension of potassium phthalimide (2.64 g, 14.21 mmol) in DMF (20 mL), 2-(2-bromoethyl)oxirane (11) (3.22 g, 21.23 mmol) was added and reacted in the microwave for 20 min at 100 °C (cooling off, pressure off). After cooling the reaction mixture was filtered and diluted with EtOAc (30 mL). After washing with H2O (2 × 10 mL) the organic phase was dried over Na2SO4 and the solvent removed under reduced pressure to afford 6b (94 %). 1H NMR (360 MHz, CDCl3): δ (ppm) = 7.87 (dd, J = 5.5 Hz, J = 3.0 Hz, 2H), 7.73 (dd, J = 5.4 Hz, J = 3.0 Hz, 2H), 3.98 - 3.83 (m, 2H), 3.05 - 2.98 (m, 1H), 2.74 (dd, J = 5.0 Hz, J = 3.9 Hz, 1H), 2.47 (dd, J = 5.0 Hz, J = 2.6 Hz, 1H),1.97 - 2.03 (m, 1H), 1.89 (dt, J = 14.2 Hz, J = 7.0 Hz, 1H). 13C NMR (151 MHz, CDCl3): δ (ppm) =169.67, 135.38, 133.53, 124.70, 51.54, 47.78, 36.56, 33.05. |
78% | In N,N-dimethyl-formamide at 100℃; for 0.333333h; microwave; |
78% | In N,N-dimethyl-formamide at 100℃; for 0.333333h; microwave irradiation; | 18 A suspension of 1.84 g (10.0 mmol) phthalimid potassium salt in 20 ml_ DMF was treated with 2.27 g (15.0 mmol) 24 in the microwave (pressure vessel, Pmax 150 W, cooling, 100 °C, 20 min). See J. Org. Chem. 1969, 34, 4060-4065. The cooled reaction mixture was filtered, diluted with EtOAc (20 mL) and was washed with H2O (2 x 10 ml_). The organic phase was dried with sodium sulphate and the volatiles were removed in vacuo to give 25 (1.68 g, 78%) as a foam, which was used without further purification. 1H NMR (CDCI3): δ 1.86 (m, 1 H), 2.00 (m, 1 H), 2.46 (m, 1 H), 2.73 (t, J 3.9, 1 H), 3.00 (m, 1 H), 3.89 (m, 2H), 7.70-7.74 (m, 2H), 7.83-7.87 (m, 2H). 13C NMR (CDCI3): δ 31.7, 35.2, 46.5, 50.4, 123.4, 132.2, 134.1, 168.4. |
In N,N-dimethyl-formamide at 100℃; for 0.333333h; Microwave irradiation; | 18 A suspension of 1.84 g (10.0 mmol) phthalimid potassium salt in 20 mL DMF was treated with 2.27 g (15.0 mmol) 24 in the microwave (pressure vessel, Pmax 150 W, cooling, 100° C., 20 min). See J. Org. Chem. 1969, 34, 4060-4065. The cooled reaction mixture was filtered, diluted with EtOAc (20 mL) and was washed with H2O (2×10 mL). The organic phase was dried with sodium sulphate and the volatiles were removed in vacuo to give 25 (1.68 g, 78%) as a foam, which was used without further purification. 1H NMR (CDCl3): δ 1.86 (m, 1H), 2.00 (m, 1H), 2.46 (m, 1H), 2.73 (t, J 3.9, 1H), 3.00 (m, 1H), 3.89 (m, 2H), 7.70-7.74 (m, 2H), 7.83-7.87 (m, 2H). 13C NMR (CDCl3): δ 31.7, 35.2, 46.5, 50.4, 123.4, 132.2, 134.1, 168.4. | |
In N,N-dimethyl-formamide at 20℃; for 12h; | ||
In N,N-dimethyl-formamide at 100℃; | INTERMEDIATE 32. 2-[2-(oxiran-2-yl)ethyl]isoindoline-l,3-dione A suspension of phthalimide potassium salt (800 mg, 4.32 mmol) in DMF (15 mL) was treated with INTERMEDIATE 31 (978 mg, 6.48 mmol), heated at 100°C overnight . The cooled reaction mixture was filtered, diluted with EtOAc and washed with H20. The organic phase was dried over sodium sulfate and the volatiles were removed in vacuo to give desired compound as foam, which was used without further purification. White foam 890 mg (95%). NMR (400 MHz, Chloroform-;/) δ 7.86 (dd, J = 5.5, 3.0 Hz, 2H), 7.76 - 7.68 (m, 2H), 3.54 (dd, J = 7.4, 5.9 Hz, 2H), 3.12 (dtd, J = 6.8, 4.2, 2.7 Hz, 1H), 2.87 (dd, J= 4.9, 4.0 Hz, 1H), 2.61 (dd, J= 4.9, 2.6 Hz, 1H), 2.19 (dtd, J= 14.8, 7.4, 4.5 Hz, 1H), 2.08 (dq, J= 14.7, 6.1 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane at 0 - 20℃; for 48h; | B.b 70 g (350 mmol) 2-(but-3-enyl)-isoindolin-1,3-dione are dissolved in dichloromethane. The solution is cooled to ca. 0° C. and a suspension of 120.8 g (350 mmol) 50% 3-chloro-peroxy-benzoic acid in dichloromethane is added under cooling. The mixture is left standing without further cooling at room temperature for two days. After addition of 250 ml saturated NaHCO3 solution the organic phase is separated and washed three times each with 200 ml saturated NaHCO3 solution and once with water. The organic phase is dried over sodium sulfate and the solvent is removed under vacuum: yield 80 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In isopropyl alcohol; at 100℃; for 0.333333h;Microwave irradiation; | General procedure: A solution of accordingly substituted commercially available phenylpiperazine (5a-f) (1.0 eq., 3.45-6.72 mmol) and 2-(2-(oxirane-2-yl)-ethyl)isoindoline-1,3-dione (6b) (1.0 eq., 3.45-6.72 mmol) in warm 2-PrOH (20 mL) were reacted in the microwave for 20 min at 100 C (cooling off, pressure off). The solvent was then removed under reduced pressure and the residue was washed with cold 2-PrOH (20 mL) to afford racemic mixtures of title compounds as yellowish-white solids in yields of 86-93 %. Rf-Value: 0.8 (MeOH / EtOAc = 1:9) |