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CAS No. : | 18424-96-9 |
Formula : | C5H9NO2 |
M.W : | 115.13 |
SMILES Code : | CN1CCOC(=O)C1 |
MDL No. : | MFCD16659615 |
InChI Key : | NMAIBUJJZUMSPH-UHFFFAOYSA-N |
Pubchem ID : | 519559 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
* 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 |
---|---|---|
98% | Stage #1: With triethyloxonium fluoroborate In dichloromethane at 20℃; Stage #2: With Lindlar's catalyst; hydrogen; sodium methylate In ethanol at 25℃; Cooling with ice |
General procedure: A solution of carboxylic acid amide (20 mmol) in dichloromethane (10 ml) is admixed with triethyloxonium tetrafluoroborate (4.18 g, 22 mmol) and stirred either (A) overnight at room temperature or (B) for 3 hours on the water bath at 40° C. under argon. Then, the mixture is concentrated in vacuo and the residue is taken up in 20 ml of absolute ethanol. An autoclave cooled in the ice bath is charged with catalyst (1 mol percent) and 10 ml of 2M sodiummethylate solution in ethanol, flushed with argon and filled with the reaction solution in ethanol. 40 bar of hydrogen are then injected in, and the mixture is stirred at 25° C. and a constant pressure until hydrogen absorption is no longer evident (1-12 h). After filtration over Celite, the filtrate is dissolved in 11 ml of 2N hydrochloric acid and washed with diethyl ether, the aqueous phase is rendered basic with 14 ml of 2N NaOH solution, the amine is extracted with diethyl ether, and the combined organic phases are dried over K2CO3. After drawing off the solvent in vacuo, virtually clean amine is obtained. (0186) The catalysts used and yields can be found in Table 6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With 5.4 wt% Au/CeO2; water; oxygen In 1,4-dioxane at 100℃; for 10 h; Schlenk technique | General procedure: A 100-mL Schlenk flask, equipped with a high-vacuumTeflon stopcock was charged with a stir bar and 70 mg of 5.4 wtpercent Au/CeO2 catalyst (3.78 mg, 0.0192 mmol Au).This was followed by the addition of 0.45 mL of ultrapurewater, 2.66 mL of 1,4-dioxane, 1.21 mL of a 404-mM stock solution of N-methylpyrrolidine (0.488 mmol)in 1,4-dioxane, and 0.67 mL of a dodecane (internal standard)stock solution (120 mM) in 1,4-dioxane. The reactionflask was purged through the side arm with oxygenfor 1 min and sealed with the stopcock. The contents ofthe flask were stirred at 80 °C in an oil bath. The moleratio of gold atoms to substrate was 1:25. GC analysis wasperformed as described in Sect. 2.7. At 3.5 h of reactiontime, a 100 percent substrate conversion was achieved with a97 percent yield of N-methyl-2-pyrrolidone. When the reactionof N-methylpyrrolidine was carried out under an air atmosphere,the same procedure was followed as above, butwithout the purge with oxygen gas. Periodic GC analysisof the reaction solution revealed a 97 percent yield of N-methyl-2-pyrrolidone after 10 h of heating at 80 °C. When the reactionwas carried out under an argon atmosphere, using theprocedure outlined in Sect. 2.8, GC analysis of the reactionsolution after 3.5 h of heating at 80 °C revealed a 4 percent yieldof N-methyl-2-pyrrolidone. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In toluene; | Example 1 - Preparation of 4-Methyl-2-Morpholinone (6621-7) To a 500-ml three-necked flask equipped with a stirrer, thermometer, and addition funnel was added 145 g of glyoxal solution (40% aqueous solution, 1 mol) in 100 g of toluene. Cool the reaction flask. Then a solution of 75.1 g of N-methylmonoethanolamine (1 mol) in 50 g of toluene was added at the temperature 5 C.-10 C. The reaction mixture was stirred for additional two hours at temperature below room temperature and then heated to reflux to azeotrope out water. The product was distilled to give 100.9 g of 4-methyl-2-morpholinone (88% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | Example 2 (6621-10) The procedure of Example 2 was followed except that the reaction was carried out at about 25 C. initially. About 91 g of 4-methyl-2-morpholinone was obtained (79% yield). This example demonstrated that lower yield was obtained when the reaction was carried out at relative higher temperature. | |
(b) Thermolysis to give 4-N-methylmorpholin-2-one 50 g of the compound (1a) are heated at 175 C. in a closed flask equipped with a stirrer until the entire product has become liquid. The liquid product is then cooled and distilled in vacuo. This gives 48 g (=96% of theory) of 4-N-methylmorpholin-2-one in the form of a colourless liquid (boiling point 56-58 C. at 0.09 mbar). Empirical formula C5 H9 NO2, molecular weight: 115. Analytical data: calculated C: 52.2%, H: 7.8%, N: 12.1%; found C: 52.2%, H: 7.8%, N: 12.1%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With osmium(VIII) oxide; In tetrahydrofuran; water; acetone; toluene; at 25℃; | Example 65 2 (R)- (3-CHLORO-4-METHANESULFONYL-PHENYL)-3-CYCLOPENTYL-N- [5- (1, 2-dihydroxy- ETHYL)-PYRAZIN-2-YL]-PROPIONAMIDE [000319] A solution of N-methyl morpholine oxide (27 mg, 0.23 mmol) and a 0.2M solution of osmium tetroxide in toluene (5 L, 0.001 mmol) in acetone (0.5 mL) and water (0.5 mL) was treated with 2 (R)- (3-CHLORO-4-METHANESULFONYL-PHENYL)-3- CYCLOPENTYL-N- (5-VINYL-PYRAZIN-2-YL)-PROPIONAMIDE (prepared as in Example 54,50 mg, 0.115 mmol). Two drops of tetrahydrofuran were added to fully dissolve the substrate, and the resulting mixture was stirred at 25C overnight. The reaction mixture was concentrated in vacuo, and the residue was treated with water (10 ML) and methylene chloride (25 mL). The organic phase was washed with a 1 N aqueous hydrochloric acid solution (10 mL), and each aqueous phase was extracted with a small portion of methylene chloride. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 12M, Silica, ethyl acetate) afforded 2 (R)- (3-CHLORO-4-METHANESULFONYL-PHENYL)-3-CYCLOPENTYL-N- [5- (1, 2- dihydroxy-ethyl) -pyrazin-2-yl] -propionamide (48 mg) as a colorless foam: (ES) +-HRMS m/e calcd for C2) H26N30SS (M+H)''468. 1355, found 468.1357. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(b) Thermolysis to give 4-N-phenylmorpholin-2-one (3b) 35.4 g (0.1 mol) of the compound (3a) are heated at 240 C. in a closed flask equipped with a stirrer until a clear liquid has been formed. The liquid is cooled and then distilled in vacuo. This gives 30 g (=84% of theory) of 4-N-methylmorpholin-2-one in the form of a clear liquid (boiling point: 146-156 C. at 0.2 mbar), which rapidly crystallises in the form of colourless leaflets on cooling. Melting point: 71-73 C. Empirical formula C10 H11 NO2. Analytical data: calculated C: 67.7%, H: 6.2%, N: 7.9%; found C: 67.7%, H: 6.1%, N: 7.9%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | General procedure: A solution of carboxylic acid amide (20 mmol) in dichloromethane (10 ml) is admixed with triethyloxonium tetrafluoroborate (4.18 g, 22 mmol) and stirred either (A) overnight at room temperature or (B) for 3 hours on the water bath at 40 C. under argon. Then, the mixture is concentrated in vacuo and the residue is taken up in 20 ml of absolute ethanol. An autoclave cooled in the ice bath is charged with catalyst (1 mol %) and 10 ml of 2M sodiummethylate solution in ethanol, flushed with argon and filled with the reaction solution in ethanol. 40 bar of hydrogen are then injected in, and the mixture is stirred at 25 C. and a constant pressure until hydrogen absorption is no longer evident (1-12 h). After filtration over Celite, the filtrate is dissolved in 11 ml of 2N hydrochloric acid and washed with diethyl ether, the aqueous phase is rendered basic with 14 ml of 2N NaOH solution, the amine is extracted with diethyl ether, and the combined organic phases are dried over K2CO3. After drawing off the solvent in vacuo, virtually clean amine is obtained. (0186) The catalysts used and yields can be found in Table 6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With 5.4 wt% Au/CeO2; water; oxygen; In 1,4-dioxane; at 100℃; under 760.051 Torr; for 10.0h;Schlenk technique;Catalytic behavior; | General procedure: A 100-mL Schlenk flask, equipped with a high-vacuumTeflon stopcock was charged with a stir bar and 70 mg of 5.4 wt% Au/CeO2 catalyst (3.78 mg, 0.0192 mmol Au).This was followed by the addition of 0.45 mL of ultrapurewater, 2.66 mL of 1,4-dioxane, 1.21 mL of a 404-mM stock solution of N-methylpyrrolidine (0.488 mmol)in 1,4-dioxane, and 0.67 mL of a dodecane (internal standard)stock solution (120 mM) in 1,4-dioxane. The reactionflask was purged through the side arm with oxygenfor 1 min and sealed with the stopcock. The contents ofthe flask were stirred at 80 C in an oil bath. The moleratio of gold atoms to substrate was 1:25. GC analysis wasperformed as described in Sect. 2.7. At 3.5 h of reactiontime, a 100 % substrate conversion was achieved with a97 % yield of N-methyl-2-pyrrolidone. When the reactionof N-methylpyrrolidine was carried out under an air atmosphere,the same procedure was followed as above, butwithout the purge with oxygen gas. Periodic GC analysisof the reaction solution revealed a 97 % yield of N-methyl-2-pyrrolidone after 10 h of heating at 80 C. When the reactionwas carried out under an argon atmosphere, using theprocedure outlined in Sect. 2.8, GC analysis of the reactionsolution after 3.5 h of heating at 80 C revealed a 4 % yieldof N-methyl-2-pyrrolidone. |
Tags: 18424-96-9 synthesis path| 18424-96-9 SDS| 18424-96-9 COA| 18424-96-9 purity| 18424-96-9 application| 18424-96-9 NMR| 18424-96-9 COA| 18424-96-9 structure
A198078 [1820735-05-4]
4-Methylmorpholin-2-one hydrochloride
Similarity: 0.97
A114032 [112257-22-4]
tert-Butyl 2-(piperazin-1-yl)acetate
Similarity: 0.76
A638168 [5616-81-9]
tert-Butyl 2-(methylamino)acetate
Similarity: 0.74
A141419 [1081523-75-2]
Ethyl 2-((2-cyanoethyl)amino)acetate hydrochloride
Similarity: 0.71
A198078 [1820735-05-4]
4-Methylmorpholin-2-one hydrochloride
Similarity: 0.97
A197732 [89531-58-8]
2-Morpholinoacetic acid hydrochloride
Similarity: 0.87
A119334 [218594-84-4]
(S)-Ethyl morpholine-3-carboxylate hydrochloride
Similarity: 0.68
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