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CAS No.: | 545445-44-1 |
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Name: | 3-Morpholino-1-(4-(2-oxopiperidin-1-yl)phenyl)-5,6-dihydropyridin-2(1H)-one |
Article Data: | 21 |
Molecular Structure: | |
Formula: | C20H25N3O3 |
Molecular Weight: | 355.437 |
Synonyms: | 3-Morpholin-4-yl-1-[4-(2-oxopiperidin-1-yl)phenyl]-5,6-dihydro-1H-pyridin-2-one; |
EINECS: | 1308068-626-2 |
Density: | 1.267 g/cm3 |
Boiling Point: | 624.979 °C at 760 mmHg |
Flash Point: | 331.775 °C |
PSA: | 53.09000 |
LogP: | 2.22420 |
morpholine
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
Conditions | Yield |
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Stage #1: 1-(piperidin-2-one-1-yl)-4-(5,6-dihydro-3-chloropyridine-2(1H)-one-1-yl)benzene With bromine; sodium hydroxide In dichloromethane; water at 25 - 35℃; for 4h; Stage #2: morpholine With triethylamine In N,N-dimethyl-formamide at 95 - 100℃; for 5h; Reagent/catalyst; Solvent; Temperature; | 95.2% |
5-Chlorovaleroyl chloride
1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
Conditions | Yield |
---|---|
Stage #1: 5-Chlorovaleroyl chloride; 1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 0 - 5℃; for 1h; Stage #2: With potassium hydroxide In dichloromethane; water at 20℃; Reagent/catalyst; Solvent; Temperature; | 94.27% |
Stage #1: 1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one With tetraethylammonium hydroxide In 1,2-dichloro-ethane at 0℃; for 0.166667h; Stage #2: 5-Chlorovaleroyl chloride In 1,2-dichloro-ethane at 0 - 85℃; for 5h; Solvent; Temperature; Reagent/catalyst; | 89% |
Stage #1: 1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one With sodium hydroxide In acetonitrile at 0℃; for 0.166667h; Green chemistry; Stage #2: 5-Chlorovaleroyl chloride In acetonitrile at 0 - 30℃; for 5h; Reagent/catalyst; Solvent; Temperature; Green chemistry; | 87.5% |
piperidin-2-one
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium hydride In dimethyl sulfoxide at 20℃; for 2h; Solvent; | 93.1% |
With copper(l) iodide; potassium tert-butylate In N,N-dimethyl-formamide at 150℃; for 16h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; | 76% |
3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
Conditions | Yield |
---|---|
With palladium diacetate; caesium carbonate In dimethyl sulfoxide at 20℃; for 6h; Reagent/catalyst; Inert atmosphere; | 93% |
1-(2-oxopiperidin-1-yl)-4-iodobenzene
3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
Conditions | Yield |
---|---|
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In dimethyl sulfoxide at 110℃; for 12h; Inert atmosphere; | 86% |
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 10 - 25℃; Inert atmosphere; | 84.5% |
With potassium tert-butylate In tetrahydrofuran at 5 - 50℃; for 8.5h; Inert atmosphere; | 3.02 g |
1-(4-iodo-phenyl)-3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one
piperidin-2-one
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
Conditions | Yield |
---|---|
With bromotris(triphenylphosphine)copper(I) In 5,5-dimethyl-1,3-cyclohexadiene Dean-Stark; Reflux; | 84% |
With potassium phosphate; bromotris(triphenylphosphine)copper(I) In 5,5-dimethyl-1,3-cyclohexadiene Reflux; Dean-Stark; | 84% |
Stage #1: 1-(4-iodo-phenyl)-3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one; piperidin-2-one In o-xylene at 25 - 30℃; for 0.166667h; Stage #2: With copper(l) iodide; potassium carbonate In o-xylene at 140 - 145℃; for 6h; | 35 g |
5-bromovaleroyl chloride
1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
Conditions | Yield |
---|---|
Stage #1: 5-bromovaleroyl chloride; 1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 40℃; for 1h; Stage #2: With sodium hydride In ethyl acetate; tert-butyl alcohol at 10 - 40℃; for 3h; Solvent; | 76% |
1-(4-iodo-phenyl)-3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one
piperidin-2-one
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
Conditions | Yield |
---|---|
With ammonium hydroxide; caesium carbonate In ethyl acetate; toluene |
1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 2 h / 5 - 50 °C / Inert atmosphere 2: potassium tert-butylate / tetrahydrofuran / 8.5 h / 5 - 50 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 10 - 25 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 10 - 25 °C / Inert atmosphere View Scheme |
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The 5,6-Dihydro-3-(4-morpholinyl)-1-[4-(2-oxo-1-piperidinyl)phenyl]-2(1H)-pyridinone, with the CAS registry number 545445-44-1, is also known as 3-Morpholin-4-yl-1-[4-(2-oxopiperidin-1-yl)phenyl]-5,6-dihydro-1H-pyridin-2-one. This chemical's molecular formula is C20H25N3O3 and molecular weight is 355.00. What's more, its systematic name is called 3-(4-Morpholinyl)-1-[4-(2-oxo-1-piperidinyl)phenyl]-5,6-dihydro-2(1H)-pyridinone.
Physical properties about 5,6-Dihydro-3-(4-morpholinyl)-1-[4-(2-oxo-1-piperidinyl)phenyl]-2(1H)-pyridinone are: (1)ACD/LogP: 1.668; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.67; (4)ACD/LogD (pH 7.4): 1.67; (5)ACD/BCF (pH 5.5): 10.89; (6)ACD/BCF (pH 7.4): 10.91; (7)ACD/KOC (pH 5.5): 192.12; (8)ACD/KOC (pH 7.4): 192.56; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 53.09 Å2; (13)Index of Refraction: 1.611; (14)Molar Refractivity: 97.409 cm3; (15)Molar Volume: 280.46 cm3; (16)Polarizability: 38.616×10-24cm3; (17)Surface Tension: 56.20 dyne/cm; (18)Density: 1.267 g/cm3; (19)Flash Point: 331.775 °C; (20)Enthalpy of Vaporization: 92.538 kJ/mol; (21)Boiling Point: 624.979 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.
You can still convert the following datas into molecular structure:
(1) SMILES: O=C1CCCCN1c2ccc(cc2)N3CC\C=C(/C3=O)N4CCOCC4
(2) InChI: InChI=1S/C20H25N3O3/c24-19-5-1-2-10-22(19)16-6-8-17(9-7-16)23-11-3-4-18(20(23)25)21-12-14-26-15-13-21/h4,6-9H,1-3,5,10-15H2
(3) InChIKey: SCVWQFDPLBFZAP-UHFFFAOYSA-N