29518-11-4

Basic information

• Product Name: 3-Morpholinone, 4-phenyl-
• Synonyms: 3-Morpholinone, 4-phenyl-;4-Phenylmorpholin-3-one;4-Phenyl-3-morpholinone
• CAS NO: 29518-11-4
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• Mol File: 29518-11-4.mol
• Article Data: 19

Chemical Properties

• Melting Point: 113-114℃
• Boiling Point: 395.2 °C at 760 mmHg
• Flash Point: 192.8 °C
• Appearance: /
• Density: 1.187
• Vapor Pressure: 1.87E-06mmHg at 25°C
• Refractive Index: 1.559
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 0.27±0.20(Predicted)
• CAS DataBase Reference: 3-Morpholinone, 4-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Morpholinone, 4-phenyl-(29518-11-4)
• EPA Substance Registry System: 3-Morpholinone, 4-phenyl-(29518-11-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 29518-11-4(Hazardous Substances Data)

Usage

Uses

4-Phenyl-3-morpholinone is used in studies to evaluate the bactericidal activity.

InChI:InChI=1/C10H11NO2/c12-10-8-13-7-6-11(10)9-4-2-1-3-5-9/h1-5H,6-8H2

Synthetic route

2-(2-chloroethoxy)-N-phenylacetamide → 4-phenyl-3-morpholinone (29518-11-4)

Conditions	Yield
With potassium carbonate In acetonitrile for 6h; Solvent; Reflux;	97%

4-Phenylmorpholine (92-53-5) → 4-phenyl-3-morpholinone (29518-11-4)

Conditions	Yield
Stage #1: 4-Phenylmorpholine With sodium dihydrogenphosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In acetonitrile at 0℃; for 0.0833333h; Stage #2: With sodium hypochlorite; sodium chlorite In water; acetonitrile	90%
With potassium permanganate; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane for 6h; phase transfer oxidation; Heating;	45%

chloroacetyl chloride (79-04-9) + 2-Anilinoethanol (122-98-5) → 4-phenyl-3-morpholinone (29518-11-4)

Conditions	Yield
With sodium hydroxide In ethanol; water at 0 - 38℃; for 2h; pH=12 - 12.5;	89%
With sodium hydroxide In ethanol; water at 2 - 43℃; pH=12 - 12.5;	80%
With sodium hydroxide In ethanol; water at 38 - 45℃; for 0.5h; pH=10 - 13; Industry scale;	68%

2-(2-((methylsulfonyl)oxy)ethoxy)-N-phenylacetamide → 4-phenyl-3-morpholinone (29518-11-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 8h;	85%

morpholine-3-one (109-11-5) + iodobenzene (591-50-4) → 4-phenyl-3-morpholinone (29518-11-4)

Conditions	Yield
With caesium carbonate at 120℃; for 14h; Goldberg Reaction; Schlenk technique; Inert atmosphere;	85%

chloroacetic acid ethyl ester (105-39-5) + 2-Anilinoethanol (122-98-5) → 4-phenyl-3-morpholinone (29518-11-4)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 38℃; for 16h; Inert atmosphere;	83%
With potassium 2-methylpropan-2-olate In tetrahydrofuran at 25℃; for 16h;	62%

2-(2-((benzenesulfonyl)oxy)ethoxy)-N-phenylacetamide → 4-phenyl-3-morpholinone (29518-11-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 8h;	81%

4-Phenylmorpholine (92-53-5) → 4-phenyl-3-morpholinone (29518-11-4) + 2-(N-phenylformamido)ethyl formate (13238-43-2)

Conditions	Yield
With ozone In acetonitrile at 25℃; for 24h; Mechanism; Solvent; Temperature; regioselective reaction;	A 46% B 8%

chloroacetic acid ethyl ester (105-39-5) + sodium-<2-anilino ethylate> → 4-phenyl-3-morpholinone (29518-11-4)

Conditions	Yield
With toluene

Acetanilid (103-84-4) → 4-phenyl-3-morpholinone (29518-11-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: nitric acid; acetic acid; sulfuric acid / 2 h / 0 - 25 °C 2: potassium carbonate / tetrahydrofuran / 4 h / 0 - 55 °C 3: potassium carbonate / acetonitrile / 6 h / Reflux View Scheme

4-nitro-aniline (100-01-6) → 4-phenyl-3-morpholinone (29518-11-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / tetrahydrofuran / 4 h / 0 - 55 °C 2: potassium carbonate / acetonitrile / 6 h / Reflux View Scheme

aniline (62-53-3) → 4-phenyl-3-morpholinone (29518-11-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 4 h / 0 - 25 °C 2: potassium carbonate / acetonitrile / 6 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 4 h / 0 - 5 °C 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine / tert-butyl methyl ether / 4 h / 0 - 5 °C 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 100 °C View Scheme
Multi-step reaction with 4 steps 1: sodium acetate; acetic acid / 0.5 h / 20 °C / Large scale 2: nitric acid; acetic acid; sulfuric acid / 2 h / 0 - 25 °C 3: potassium carbonate / tetrahydrofuran / 4 h / 0 - 55 °C 4: potassium carbonate / acetonitrile / 6 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: acetone / 15 h / Cooling with ice 2: potassium tert-butylate / tetrahydrofuran / 16 h / 38 °C / Inert atmosphere View Scheme

oxirane (75-21-8) + aniline (62-53-3) → 4-phenyl-3-morpholinone (29518-11-4)

Conditions	Yield
Stage #1: oxirane; aniline Stage #2: With potassium carbonate In N,N-dimethyl-formamide at 0 - 60℃; for 4h;

4-phenyl-3-morpholinone (29518-11-4) → 4-(4-nitrophenyl)-3-morpholinone (446292-04-2)

Conditions	Yield
With nitric acid; acetic anhydride at 0 - 25℃; for 5h;	85%
With sulfuric acid; nitric acid at -10℃; for 1h;	83%
With sulfuric acid; nitric acid at -10℃; for 1h;	83%

4-phenyl-3-morpholinone (29518-11-4) → 4-(4-bromophenyl)morpholin-3-one (634905-12-7)

Conditions	Yield
With bis-[(trifluoroacetoxy)iodo]benzene; sodium bromide In ethanol at 25℃; for 12h; Green chemistry; regioselective reaction;	60%

4-phenyl-3-morpholinone (29518-11-4) + ethyl 4-methoxybenzoate (94-30-4) → 2-(4-methoxybenzoyl)-4-phenylmorpholin-3-one

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at 0 - 20℃; Claisen Condensation; Inert atmosphere;	42%

4-phenyl-3-morpholinone (29518-11-4) + benzaldehyde (100-52-7) → 2-<1-hydroxy-1-phenylmethyl>-4-phenyl-3-morpholinone (353268-54-9)

Conditions	Yield
With lithium diisopropyl amide 1.) 30 min., -78 deg C, THF, 2.) 1 h, -78 to -30 deg C; Yield given. Multistep reaction;

4-phenyl-3-morpholinone (29518-11-4) + benzaldehyde (100-52-7) → anti-2-(1-hydroxy-1-phenylmethyl)-4-phenyl-3-morpholinone + syn-2-(1-hydroxy-1-phenylmethyl)-4-phenyl-3-morpholinone

Conditions	Yield
Stage #1: 4-phenylmorpholin-3-one With lithium diisopropyl amide In tetrahydrofuran; hexane at -80℃; for 0.25h; Metallation; Stage #2: benzaldehyde In tetrahydrofuran at -80℃; for 0.25h; α-hydroxyalkylation; Title compound not separated from byproducts;

4-phenyl-3-morpholinone (29518-11-4) → 4-(4-aminophenyl)morpholin-3-one (438056-69-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid; sulfuric acid / sulfolane / 2 h / -5 - 30 °C 2: hydrogen / Raney Ni / methanol / 24 h / 40 - 50 °C View Scheme
Multi-step reaction with 2 steps 1: nitric acid; sulfuric acid / 1 h / -10 °C 2: hydrogen / 5% Pd(II)/C(eggshell) / water; tetrahydrofuran / 6.5 h / 70 °C / 2250.23 Torr View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid / water 2: 5%-palladium/activated carbon; hydrogen / ethanol / 40 °C View Scheme

4-phenyl-3-morpholinone (29518-11-4) → Rivaroxaban (366789-02-8)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: nitric acid; sulfuric acid / sulfolane / 2 h / -5 - 30 °C 2.1: hydrogen / Raney Ni / methanol / 24 h / 40 - 50 °C 3.1: water / ethanol / 36 h / 60 °C / Industry scale 4.1: toluene / 3 h / Industry scale; Reflux 5.1: methylamine / ethanol / 4 h / 65 °C / Industry scale 5.2: 58 - 60 °C / pH 2.7 / Industry scale 6.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Industry scale 6.2: 2.5 h / 0 - 25 °C View Scheme
Multi-step reaction with 8 steps 1.1: nitric acid; sulfuric acid / 1 h / -10 °C 2.1: hydrogen / 5% Pd(II)/C(eggshell) / water; tetrahydrofuran / 6.5 h / 70 °C / 2250.23 Torr 3.1: sodium hydrogencarbonate / water; acetone / 4 h / 20 °C 4.1: lithium tert-butoxide / tetrahydrofuran / 24 h / 20 °C 5.1: triethylamine / dichloromethane / 4 h / 20 °C 6.1: isopropyl alcohol / 12 h / 120 °C 7.1: triethylamine / dichloromethane / 24 h / 20 °C 8.1: hydrogenchloride / ethyl acetate / 2 h / 55 °C 8.2: pH 9 View Scheme
Multi-step reaction with 7 steps 1.1: nitric acid; sulfuric acid / 1 h / -10 °C 2.1: hydrogen / 5% Pd(II)/C(eggshell) / water; tetrahydrofuran / 6.5 h / 70 °C / 2250.23 Torr 3.1: sodium hydrogencarbonate / water; acetone / 4 h / 20 °C 4.1: lithium tert-butoxide / tetrahydrofuran / 24 h / 20 °C 5.1: triethylamine / dichloromethane / 4 h / 20 °C 6.1: isopropyl alcohol / 12 h / 120 °C 7.1: triethylamine / toluene / 2 h / 120 °C 7.2: 4 h / 55 °C 7.3: 20 °C / pH 9 View Scheme

4-phenyl-3-morpholinone (29518-11-4) → 4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one (446292-10-0)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: nitric acid; sulfuric acid / sulfolane / 2 h / -5 - 30 °C 2.1: hydrogen / Raney Ni / methanol / 24 h / 40 - 50 °C 3.1: water / ethanol / 36 h / 60 °C / Industry scale 4.1: toluene / 3 h / Industry scale; Reflux 5.1: methylamine / ethanol / 4 h / 65 °C / Industry scale 5.2: 58 - 60 °C / pH 2.7 / Industry scale View Scheme
Multi-step reaction with 6 steps 1: sulfuric acid; nitric acid / water 2: 5%-palladium/activated carbon; hydrogen / ethanol / 40 °C 3: toluene / 20 °C / Reflux 4: MgI2*etherate / tetrahydrofuran / 20 - 80 °C / Inert atmosphere 5: sodium azide / N,N-dimethyl-formamide / 12 h / 85 °C 6: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 12 h View Scheme

4-phenyl-3-morpholinone (29518-11-4) → 2-((2R)-2-hydroxy-3-{[4-(3-oxo-4-morpholinyl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione (446292-07-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: nitric acid; sulfuric acid / sulfolane / 2 h / -5 - 30 °C 2: hydrogen / Raney Ni / methanol / 24 h / 40 - 50 °C 3: water / ethanol / 36 h / 60 °C / Industry scale View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid; nitric acid / 2.5 h / 0 - 5 °C 2: hydrogen; palladium on activated charcoal / dichloromethane / 25 - 80 °C / Inert atmosphere; Autoclave 3: 18 h / 75 - 80 °C View Scheme
Multi-step reaction with 3 steps 1.1: sulfuric acid / 0.25 h / 0 - 5 °C 1.2: 2.5 h / 0 - 5 °C 2.1: palladium on activated charcoal; hydrogen / dichloromethane / 75 - 80 °C / 3750.38 Torr / Autoclave; Inert atmosphere 3.1: ethanol / 18 h / 75 - 80 °C View Scheme

4-phenyl-3-morpholinone (29518-11-4) → 2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione (446292-08-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: nitric acid; sulfuric acid / sulfolane / 2 h / -5 - 30 °C 2: hydrogen / Raney Ni / methanol / 24 h / 40 - 50 °C 3: water / ethanol / 36 h / 60 °C / Industry scale 4: toluene / 3 h / Industry scale; Reflux View Scheme
Multi-step reaction with 4 steps 1: sulfuric acid; nitric acid / 2.5 h / 0 - 5 °C 2: hydrogen; palladium on activated charcoal / dichloromethane / 25 - 80 °C / Inert atmosphere; Autoclave 3: 18 h / 75 - 80 °C 4: dmap / dichloromethane / 40 - 45 °C View Scheme
Multi-step reaction with 7 steps 1: sulfuric acid; nitric acid / 2.5 h / 0 - 5 °C 2: hydrogen; palladium on activated charcoal / dichloromethane / 25 - 80 °C / Inert atmosphere; Autoclave 3: ethanol / 12 h / 75 - 80 °C 4: dmap / dichloromethane / 40 - 45 °C 5: water; sodium hydroxide / methanol / 1 h / 60 - 65 °C 6: triethylamine / dichloromethane / 24 h / 25 - 35 °C 7: potassium carbonate / N,N-dimethyl-formamide / 10 h / 25 - 45 °C View Scheme
Multi-step reaction with 4 steps 1.1: sulfuric acid / 0.25 h / 0 - 5 °C 1.2: 2.5 h / 0 - 5 °C 2.1: palladium on activated charcoal; hydrogen / dichloromethane / 75 - 80 °C / 3750.38 Torr / Autoclave; Inert atmosphere 3.1: ethanol / 18 h / 75 - 80 °C 4.1: dmap / dichloromethane / 40 - 45 °C View Scheme
Multi-step reaction with 7 steps 1.1: sulfuric acid / 0.25 h / 0 - 5 °C 1.2: 2.5 h / 0 - 5 °C 2.1: palladium on activated charcoal; hydrogen / dichloromethane / 75 - 80 °C / 3750.38 Torr / Autoclave; Inert atmosphere 3.1: water; ethanol / 12 h / 25 - 80 °C 4.1: dmap / dichloromethane / 25 - 45 °C 5.1: sodium hydroxide; water / methanol / 1 h / 25 - 65 °C 6.1: triethylamine / dichloromethane / 24 h / 25 - 35 °C 7.1: hydrogenchloride; potassium carbonate / N,N-dimethyl-formamide / 10 h / 25 - 45 °C View Scheme

4-phenyl-3-morpholinone (29518-11-4) → [4-(3-oxo-morpholin-4-yl)phenyl]carbamic acid benzyl ester (1313613-18-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: nitric acid; sulfuric acid / 1 h / -10 °C 2: hydrogen / 5% Pd(II)/C(eggshell) / water; tetrahydrofuran / 6.5 h / 70 °C / 2250.23 Torr 3: sodium hydrogencarbonate / water; acetone / 4 h / 20 °C View Scheme

4-phenyl-3-morpholinone (29518-11-4) → 4-{4-[(5R)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one (1117893-60-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: nitric acid; sulfuric acid / 1 h / -10 °C 2: hydrogen / 5% Pd(II)/C(eggshell) / water; tetrahydrofuran / 6.5 h / 70 °C / 2250.23 Torr 3: sodium hydrogencarbonate / water; acetone / 4 h / 20 °C 4: lithium tert-butoxide / tetrahydrofuran / 24 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: sulfuric acid; nitric acid / 2.5 h / 0 - 5 °C 2: hydrogen; palladium on activated charcoal / dichloromethane / 25 - 80 °C / Inert atmosphere; Autoclave 3: ethanol / 12 h / 75 - 80 °C 4: dmap / dichloromethane / 40 - 45 °C 5: water; sodium hydroxide / methanol / 1 h / 60 - 65 °C View Scheme
Multi-step reaction with 5 steps 1.1: sulfuric acid / 0.25 h / 0 - 5 °C 1.2: 2.5 h / 0 - 5 °C 2.1: palladium on activated charcoal; hydrogen / dichloromethane / 75 - 80 °C / 3750.38 Torr / Autoclave; Inert atmosphere 3.1: water; ethanol / 12 h / 25 - 80 °C 4.1: dmap / dichloromethane / 25 - 45 °C 5.1: sodium hydroxide; water / methanol / 1 h / 25 - 65 °C View Scheme

4-phenyl-3-morpholinone (29518-11-4) → R-(2-oxo-3-((4-(3-oxo-morpholinyl)phenyl)oxazolidin-5-yl))methylmethanesulfonate (1117893-61-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: nitric acid; sulfuric acid / 1 h / -10 °C 2: hydrogen / 5% Pd(II)/C(eggshell) / water; tetrahydrofuran / 6.5 h / 70 °C / 2250.23 Torr 3: sodium hydrogencarbonate / water; acetone / 4 h / 20 °C 4: lithium tert-butoxide / tetrahydrofuran / 24 h / 20 °C 5: triethylamine / dichloromethane / 4 h / 20 °C View Scheme

4-phenyl-3-morpholinone (29518-11-4) → 4-(4-((S)-5-(tert-butylaminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one (1313613-19-2)

Conditions	Yield
Multi-step reaction with 6 steps 1: nitric acid; sulfuric acid / 1 h / -10 °C 2: hydrogen / 5% Pd(II)/C(eggshell) / water; tetrahydrofuran / 6.5 h / 70 °C / 2250.23 Torr 3: sodium hydrogencarbonate / water; acetone / 4 h / 20 °C 4: lithium tert-butoxide / tetrahydrofuran / 24 h / 20 °C 5: triethylamine / dichloromethane / 4 h / 20 °C 6: isopropyl alcohol / 12 h / 120 °C View Scheme
Multi-step reaction with 7 steps 1: nitric acid; sulfuric acid / 1 h / -10 °C 2: hydrogen / 5% Pd(II)/C(eggshell) / water; tetrahydrofuran / 6.5 h / 70 °C / 2250.23 Torr 3: sodium hydrogencarbonate / water; acetone / 4 h / 20 °C 4: lithium tert-butoxide / tetrahydrofuran / 24 h / 20 °C 5: triethylamine / dichloromethane / 4 h / 20 °C 6: N,N-dimethyl-formamide / 24 h / 80 °C 7: sodium hydrogencarbonate / ethyl acetate View Scheme

4-phenyl-3-morpholinone (29518-11-4) → 4-(4-((S)-5-(tert-octylaminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one (1313613-22-7)

Conditions	Yield
Multi-step reaction with 6 steps 1: nitric acid; sulfuric acid / 1 h / -10 °C 2: hydrogen / 5% Pd(II)/C(eggshell) / water; tetrahydrofuran / 6.5 h / 70 °C / 2250.23 Torr 3: sodium hydrogencarbonate / water; acetone / 4 h / 20 °C 4: lithium tert-butoxide / tetrahydrofuran / 24 h / 20 °C 5: triethylamine / dichloromethane / 4 h / 20 °C 6: isopropyl alcohol / 0 - 120 °C View Scheme

4-phenyl-3-morpholinone (29518-11-4) → 5-chloro-N-tert-butyl-N-{[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxazolidin-5-yl]methyl}thiophene-2-carboxamide (1313613-21-6)

Conditions	Yield
Multi-step reaction with 7 steps 1: nitric acid; sulfuric acid / 1 h / -10 °C 2: hydrogen / 5% Pd(II)/C(eggshell) / water; tetrahydrofuran / 6.5 h / 70 °C / 2250.23 Torr 3: sodium hydrogencarbonate / water; acetone / 4 h / 20 °C 4: lithium tert-butoxide / tetrahydrofuran / 24 h / 20 °C 5: triethylamine / dichloromethane / 4 h / 20 °C 6: isopropyl alcohol / 12 h / 120 °C 7: triethylamine / dichloromethane / 24 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1: nitric acid; sulfuric acid / 1 h / -10 °C 2: hydrogen / 5% Pd(II)/C(eggshell) / water; tetrahydrofuran / 6.5 h / 70 °C / 2250.23 Torr 3: sodium hydrogencarbonate / water; acetone / 4 h / 20 °C 4: lithium tert-butoxide / tetrahydrofuran / 24 h / 20 °C 5: triethylamine / dichloromethane / 4 h / 20 °C 6: N,N-dimethyl-formamide / 24 h / 80 °C 7: sodium hydrogencarbonate / ethyl acetate 8: triethylamine / dichloromethane / 24 h / 20 °C View Scheme

4-phenyl-3-morpholinone (29518-11-4) → 5-chloro-N-tert-octyl-N-{[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxazolidin-5-yl]methyl}thiophene-2-carboxamide (1313613-23-8)

Conditions

Yield

Multi-step reaction with 7 steps 1: nitric acid; sulfuric acid / 1 h / -10 °C 2: hydrogen / 5% Pd(II)/C(eggshell) / water; tetrahydrofuran / 6.5 h / 70 °C / 2250.23 Torr 3: sodium hydrogencarbonate / water; acetone / 4 h / 20 °C 4: lithium tert-butoxide / tetrahydrofuran / 24 h / 20 °C 5: triethylamine / dichloromethane / 4 h / 20 °C 6: isopropyl alcohol / 0 - 120 °C 7: dmap; triethylamine / toluene / 10 h / Inert atmosphere; Reflux View Scheme

4-phenyl-3-morpholinone (29518-11-4) → 4-(4-((S)-5-(tert-butylaminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one methanesulfonic salt (1313613-20-5)

Conditions	Yield
Multi-step reaction with 6 steps 1: nitric acid; sulfuric acid / 1 h / -10 °C 2: hydrogen / 5% Pd(II)/C(eggshell) / water; tetrahydrofuran / 6.5 h / 70 °C / 2250.23 Torr 3: sodium hydrogencarbonate / water; acetone / 4 h / 20 °C 4: lithium tert-butoxide / tetrahydrofuran / 24 h / 20 °C 5: triethylamine / dichloromethane / 4 h / 20 °C 6: N,N-dimethyl-formamide / 24 h / 80 °C View Scheme

4-phenyl-3-morpholinone (29518-11-4) → 4-{4-[(5R)-5-(chloromethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one (1252018-28-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid; nitric acid / water 2: 5%-palladium/activated carbon; hydrogen / ethanol / 40 °C 3: toluene / 20 °C / Reflux 4: MgI2*etherate / tetrahydrofuran / 20 - 80 °C / Inert atmosphere View Scheme

4-phenyl-3-morpholinone (29518-11-4) → 4-{4-[(5R)-5-(azidomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one (1349248-79-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: sulfuric acid; nitric acid / water 2: 5%-palladium/activated carbon; hydrogen / ethanol / 40 °C 3: toluene / 20 °C / Reflux 4: MgI2*etherate / tetrahydrofuran / 20 - 80 °C / Inert atmosphere 5: sodium azide / N,N-dimethyl-formamide / 12 h / 85 °C View Scheme

Upstream product

• 79-04-9 chloroacetyl chloride 
• 122-98-5 2-Anilinoethanol 
• 109-11-5 morpholine-3-one 
• 591-50-4 iodobenzene 
• 75-21-8 oxirane 
• 62-53-3 aniline 
• 100-01-6 4-nitro-aniline 
• 103-84-4 Acetanilid 
• 92-53-5 4-Phenylmorpholine 
• 105-39-5 chloroacetic acid ethyl ester 

Downstream Products

• 634905-12-7 4-(4-bromophenyl)morpholin-3-one 
• 1430407-73-0 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidine-3-yl]phenyl}morpholin-3-one oxalate 
• 1424942-80-2 (R)-(2-oxo-3-(4-(3-oxo-morpholino)phenyl)oxazolidin-5-yl)methyl 4-methylbenzene sulfonate 
• 1446022-15-6 butyric acid-2-oxo-5(R)-3-[4-(3-oxomorpholin-4-yl)-phenyl]oxazolidin-5-yl-methyl ester 
• 1446022-14-5 butyric acid-2(R)-2-hydroxy-3-[4-(3-oxo-morpholin-4-yl)phenylamino]-propyl ester 
• 1325210-64-7 4-(4-isocyanatophenyl)morpholin-3-one 
• 1349248-79-8 4-{4-[(5R)-5-(azidomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one 
• 1252018-28-2 4-{4-[(5R)-5-(chloromethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one 
• 1313613-20-5 4-(4-((S)-5-(tert-butylaminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one methanesulfonic salt 

Relevant articles and documents

Activated charcoal supported copper nanoparticles: A readily available and inexpensive heterogeneous catalyst for the N-arylation of primary amides and lactams with aryl iodides

A novel heterogeneous copper catalyst has been developed by supporting copper nanoparticles on activated charcoal via in situ reducing copper(II) with aqueous hydrazine as reductant. The characterization of Cu/C catalyst showed that the Cu0 nano-particles were formed on the surface of charcoal. This catalyst displayed good catalytic activities toward the N-arylation of primary amides and lactams with aryl iodides.

The preparation method of the [...] (by machine translation)

The invention provides a method for preparing [...], using 4 - (4 - aminophenyl) - 3 - morpholone and 5 - chloro - N - (2 - ethylene oxide-based methyl) - 2 - thiophene carboxamide reaction to obtain 5 - [...] - 2 - {(R)- 2 - hydroxy - 3 - [4 - (3 - oxo - 4 - morpholinyl) phenyl amino] - propyl} amide, then adding N, N' - carbonyl di-imidazole, 4 - dimethylamino pyridine, begins to stir, heating reaction to obtain the - 5 - chloro - N - (( (5 S) - 2 - oxo - 3 - (4 - (3 - oxo-morpholine - 4 - yl) phenyl) - 1, 3 - Oxacillin - 5 - yl) methyl) thiophene - 2 - carboxamide. The technique of the invention route after the condition is optimized, mild reaction, high yield. (by machine translation)

A 4 - (4-amino-phenyl) - 3-morpholinon process and intermediates for the preparation of

The invention belongs to the technical field of preparing 4-(4-amino phenyl)-3-morpholone, especially relates to a preparation method of 4-(4-amino phenyl)-3-morpholone and intermediate of the 4-(4-amino phenyl)-3-morpholone. The method comprises the following steps: amide intermediate cyclization, nitration, and reduction. The raw material aniline is a low-cost chemical, and the acylation raw material is easy to synthetize and low in cost. Compared with documents in which acylation is directly carried out after nitration, in the method disclosed by the invention, nitration is carried out after acylation, so that the method disclosed by the invention has the advantages no substituted group protection, high selectivity, less steps, high yield and the like. The preparation process does not need harsh reaction conditions such as high pressure, high temperature and deep cooling and also does not need an expensive palladium-carbon catalyst, and meets the requirements of industrial production.