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CAS No. : | 65451-89-0 | MDL No. : | MFCD06761896 |
Formula : | C10H15NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 181.23 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P264-P270-P280-P302+P352-P305+P351+P338-P310-P330-P332+P313-P362-P501 | UN#: | 2735 |
Hazard Statements: | H302-H315-H318 | 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 |
---|---|---|
With 1,3-dimethylbarbituric acid;tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine; In dichloromethane; for 3h;Heating / reflux; | D. A 50-mL round bottom flask was charged with Compound 18d (0.40 g, 1.53 mmol) and dichloromethane (8.0 ml_). Pd2(dba)3- CHCI3 (0.16 g, 0.15 mmol), triphenylphosphine (0.16 g, 6.1 mmol), and 1 ,3-dimethylbarbituric acid (0.79 g, 5.06 mmol) were added and the mixture was heated to reflux for 3 h. The mixture was cooled to room temperature, transferred to a separatory funnel, and extracted with 1 N HCI (50 ml_). The aqueous layer was basified with 3N NaOH and extracted with ethyl acetate (200 ml_). The organic layer was dried with MgSO4 and filtered through Celite to give Compound 18e as a white solid. 1H NMR (300 MHz, CDCI3) δ 6.74-6.85 (m, 3 H), 3.96-4.08 (m, 1 H), 3.83 (m, 3 H), 3.80 (m, 3 H), 1.87-1.97 (bs, 2 H), and 1.31 (d, J = 6.6 Hz, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | at 100 - 150℃;Green chemistry; | General procedure: An amount of 327.43 mg (1.1 mmol) of phthalic anhydrideand 243.56 mg (1 mmol) of phenylethylamine were placedinto a 50-mL round-bottom flask. The mixture was stirredand heated to gentle boil 100-150 C for 5-10 min. Thereaction was cooled at room temperature and monitored byTLC. Then the appropriate solvent (40 mL) was added andthe reaction was sonicated until a white powder formed. Theprecipitate was filtered, dissolved in acetone and precipitatedagain with water (pH 13). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | at 150℃;Green chemistry; | General procedure: An amount of 433.80 mg (1.6435 mmol) of α,α′-dibromo-oxyleneand 199.16 mg (1.6435 mmol) phenylethylaminewere placed into a 50-mL round-bottom flask. The mixturewas stirred and heated to gentle boil 150-250 C for 5-10min. The reaction was cooled at room temperature andmonitored by TLC. Afterwards, ethyl acetate (40 mL) wasadded and the reaction was sonicated until a white powder(hydrobromide) formed. The precipitate was filtered andwashed twice with acetone. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With lipase B from Candida antarctica immobilized on acrylic beads; In toluene; at 30℃; for 8h;Resolution of racemate; Enzymatic reaction; | General procedure: Into a screw cap reaction vial were added a mixture of dry toluene (1.0 mL), immobilized CaLB enzyme (15.0 mg, CaLB-CV-T2-150), the corresponding racemic amine rac-1a-d (0.778 mmol) and the corresponding isopropyl 2-alkoxyacetate 2A-D (1.0 equiv., 0.778 mmol). The reaction mixture was shaken (750 rpm) at 30 C and monitored by taking samples (20 mL) after different reaction times (0.25, 0.5, 1, 2, 3, 4, 6, 8 h). After 8 h, the reactions were worked up. |
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