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CAS No. : | 503615-03-0 | MDL No. : | MFCD19440872 |
Formula : | C15H17N3O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LBFAEOWNWSDWRZ-UHFFFAOYSA-N |
M.W : | 303.31 | Pubchem ID : | 21936809 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
66% | Stage #1: Cooling with ice Stage #2: for 2 h; Reflux |
Compound 5 (33 g, 0.15 mol), Phosphorus pentachloride (109 g, 0.52 mol), The reaction solution was poured into 500 ml of ice water, the solution was separated, and the aqueous layer was extracted three times with chloroform (100 ml). The reaction mixture was extracted with ethyl acetate, The organic phase was combined, washed once with 500 ml of saturated brine, and dried over anhydrous magnesium sulfate. Filtered and the solvent evaporated to give 57 g of a yellow solid. The solid (57g) added to the reaction flask, morpholine 307ml added, slowly heated to reflux, the reaction 2h, cooling to morpholine hydrochloride solid precipitation, add water 600ml precipitated product, dried yellow solid 30g, two-step reaction total income Rate of 66percent. |
53% | Stage #1: With phosphorus pentachloride In chloroform at 20℃; Stage #2: for 2 h; Heating / reflux |
Part B: The lactam (44.68 g, 203.1 mmol) was dissolved in 550 mL of CHCl3 and stirred at rt for 5 minutes then PCl5 (143.6 g, 690.5 mmol) was added portionwise followed by an additional 100 mL of CHCl3. The nitrogen outlet was replaced with a scrubber system consisting of 1N NaOH and the reaction was refluxed for 2 hours. The reaction was then cooled and slowly poured into a 4-liter beaker containing 860 mL of water and 250 mL of CHCl3 already cooled to 0° C. The mixture was stirred about 1/2 hour then transferred to a separatory funnel and separated. The organic layer was dried over sodium sulfate and evaporated to give the chlorinated intermediate (51.9 g, 90percent yield). The intermediate was added to morpholine (172.6 g, 1.98 mol) neat and heated to reflux for 2 hours then cooled. Next 500 mL of CHCl3 and a mixture of 500 mL saturated NaH2PO4 monohydrate and 50 mL of conc. HCl was added. The reaction was transferred to a separatory funnel and washed with saturated NaH2PO4 monohydrate then water and dried over sodium sulfate and evaporated The residue was recrystallized in EtOAc to yield the enamine (28.46 g, 53percent yield) LRMS (ES+) 304.8 (M+H)+. |
16 g | Stage #1: With phosphorus pentachloride In dichloromethane at 0 - 30℃; for 2.5 h; Stage #2: at 125 - 130℃; for 1 h; |
In 3 L 4-neck round bottom flask equipped with mechanical stirrer, thermometer and addition funnel, methylene dichloride (120 mL) and PC15 (85•15 gm) were added at 25°C. The reaction mixture was stirred for 15 min and cooled to 0°C to 5°C. A solution of l-(4-nitrophenyl)piperidin-2-one (3 gm) in methylene dichloride (120 ml) was added and stirred for 30 min. The reaction mixture was raised to 25°C to 30°C, stirred for 2 hours and cooled to 0°C to 5°C. Water (600 mL) was added and stirred to separate the layer. The separated methylene dichloride was dried over anhydrous sodium sulphate and distilled under vacuum at 45°C to 50°C. Morpholine (156 mL) was added and stirred for 30 min followed by heating at 125-130°C for 30 min. The reaction mixture was cooled to 70°C to 75°C and distilled to remove excess morpholine under vacuum at 70°C to 75°C and cooled to 55°C to 60°C. Methanol (120 mL) and water (60 mL) was added at 55°C to 60°C and cooled to 25°C to 30°C. The reaction mixture was stirred for 30 mins and filtered. The solid was washed with water and dried at 50°C to 55°C under vacuum to obtain 16 gm of 3 -morpholino- 1- (4-nitrophenyl)-5,6-dihydropyridin-2(IH)-one (VI) |
16 g | Stage #1: With phosphorus pentachloride In dichloromethane at 0 - 30℃; for 2.5 h; Stage #2: at 125 - 130℃; for 1 h; |
In 3 L 4-neck round bottom flask equipped with mechanical stirrer, thermometer and addition funnel, methylenedichloride (120 mE) and PC15(85 .15 gm) were added at 25° C. The reaction mixture was stirred for 15 mm and cooled to 0° C. to 5° C. A solution of 1 -(4-nitrophenyl)piperidin- 2-one (30 gm) in methylene dichioride (120 ml) was added and stirred for 30 mm. The reaction mixture was raised to25° C. to 30° C., stirred for 2 hours and cooled to 0° C. to5° C. Water (600 mE) was added and stirred to separate the layer. The separated methylene dichloride was dried over anhydrous sodium sulphate and distilled under vacuum at 45°C. to 50°C. Morpholine (156 mE) was added and stirred for 30 mm followed by heating at 125-130° C. for 30 mm. The reaction mixture was cooled to 70° C. to 75° C. and distilled to remove excess morpholine under vacuum at 70° C. to 75° C. and cooled to 55° C. to 60° C. Methanol (120 mE) and water (60 mE) was added at 55° C. to 60° C. and cooled to 25° C. to 30° C. The reaction mixture was stirred for 30 mins and filtered. The solid was washed with water and dried at 50° C. to 55° C. under vacuum to obtain 16 gm of 3-morpholino-1 -(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one (VII). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.4% | at 120℃; for 2 h; Inert atmosphere | The 1c (19.0g, 65.7mmol) was dissolved in morpholine (100ml) to obtain a reaction mixture,reaction mixture at reflux for 2 hours 120 °C , reaction progress was followed by thin layer chromatography, the reaction was completed, vacuum distillation most morpholine was removed, the residue as a yellow solid which was washed with water stirred 1 hour, filtered, the filter cake washed three times, air-dried and dried 24 hours give 1d (18.0g, yellow solid), yield: 90.4percent |
87.6% | at 130℃; for 1.5 h; | A mixture of compound 3 (50.3 g, 0.17 mol) and morpholine(200 mL) was stirred at 130 °C for 1.5 h, and then cooled to room temperature. The solvent was removed under vacuum,and the precipitate was collected by filtration and washed with water to afford the desired product 4 as a yellow solid (46.3 g,87.6percent), Mp: 157.3–160.3 C; MS (ESI) m/z (percent): 304.0 [M+H]+,326.0 [M+Na]+. 1H NMR (400 MHz, DMSO-d6) d 8.21 (d,J = 3.0 Hz, 1H, Ar-H), 8.18 (d, J = 3.0 Hz, 1H, Ar-H), 7.62 (d,J = 3.0 Hz, 1H, Ar-H), 7.59 (d, J = 3.0 Hz, 1H, Ar-H), 5.77 (t,J = 4.5 Hz, 1H, CCH–C), 3.79 (t, J = 7.5 Hz, 2H, N–CH2–C), 3.62–3.59 (m, 4H, O–CH2–C), 2.73–2.77 (m, 4H, N–CH2–C), 2.47–2.41(m, 2H, C–CH2-C). |
64.5% | at 130℃; for 5 h; | Compound III was added to a 500 mL eggplant flask(40 g, 0.14 mol),Morpholine (160 ml, 1.84 mol),The reaction was warmed to 130 ° C for 5 h. The morpholine was recovered under reduced pressure, and 400 mL of water was added to the residue. After stirring for 30 min, suction filtration and drying gave crude product57.8g, 8 times of ethyl acetate was recrystallized to give the product as a light yellow solid, 27.2g, m.p. 158-160°C, yield 64.5percent. |
85.73 g | for 1 h; Reflux | PCl5 (212.5 g, 1.02 mol) was slowly added to a solution of the product of example-II (75 g, 0.340 mol) in Toluene (225 mL) at 25-30° C. The resulting mixture was gradually heated to 75-80° C. for 1 h and poured into ice water (1 L), maintaining temperature below 10° C. The quenched mass was stirred at 0-5° C. for 1 h and filtered under suction. The pale yellow colored product was dried in air oven at 55°-60° C. for 6-8 hrs. The dried product was dissolved in DMF (130 ml) and morpholine (130 ml) and refluxed for 1 h. The reaction mixture was cooled to 60° C. and water was added to the reaction mass at the same temperature. The resulting slurry was filtered under suction, washed with water to get a yellow solid. Recrystallization of the solid from MeOH afforded the desired product as an off-white solid. Yield: 85.73 g, 83.0percent; MP 158-160° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11.2 g | With triethylamine In tetrahydrofuran for 46 h; Inert atmosphere; Reflux | 3-Chloro-l-(4-nitrophenyl)-5,6-dihydropyridin-2(lH)-one (11.1 g, 43.9 mmol) was suspended in dry Tetrahydrofuran (45 mL). Morpholine (3.8 g, 43.9 mmol, 1 eq.) and triethylamine (8.9 g, 87.9 mmol) were added successively. Resulting mixture was heated to reflux under nitrogen atmosphere. Additional Morpholine (1.5 molpercent) and triethylamine (3 molpercent) were added after 22 h. After next 6 h, reaction mixture still contained 0.5percent of the starting compound. Morpholine (0.5 molpercent) and triethylamine (1 molpercent) were added and resulting mixture was further heated to reflux for 18 h. THF was evaporated and the solid residue was mixed with water (25 mL) and Ethyl acetate (25 mL). Solid material was collected, washed with water (2x 15 mL) and Ethyl acetate (2x 15 mL) to give 11.2 g of yellow solid. |
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