4-[4-[(5S)-5-(Aminomethyl)-2-oxo-3-oxazolidinyl]phenyl]-3-morpholinone hydrochloride supplier

Name
(S)-4-(4-(5-(Aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one.HCl
EINECS 618-311-0
CAS No. 898543-06-1
Article Data20
CAS DataBase
Density
Solubility 184.9g/L at 20℃
Melting Point 250
Formula C₁₄H₁₇N₃O₄^.HCl
Boiling Point 593.9 °C at 760 mmHg
Molecular Weight 327.768
Flash Point 313 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4-[4-[(5S)-5-(Aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholin-3-one hydrochloride;(S)-4-(4-(5-(Aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one hydrochloride;3-Morpholinone, 4-[4-[(5S)-5-(aminomethyl)-2-oxo-3-oxazolidinyl]phenyl]-, monohydrochloride (9CI);
PSA 85.10000
LogP 1.96600

Synthetic route

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

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Stage #1: 2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione With methylamine In N,N-dimethyl-formamide at 60 - 65℃; for 5h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 40℃; Temperature; Solvent;	96%
Stage #1: 2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione With methylamine In methanol; water at 25 - 65℃; for 5h; Stage #2: With hydrogenchloride In methanol; water at 25 - 30℃; for 0.5h; pH=1 - 2; Temperature;	92%
Stage #1: 2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione With methylamine In ethanol; water at 40 - 60℃; for 8h; Stage #2: With hydrogenchloride In water at 15℃; for 2h;	89.7%

: 1414932-73-2
(S)-4-(4-{5-[(benzylidene-amino)-methyl]-2-oxo-oxazolidine-3-yl}-phenyl)-morpholin-3-one

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water at 0 - 15℃; for 0.75h; pH=2; Temperature; pH-value;	92.4%

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

: 74-89-5
methylamine

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Stage #1: 2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione; methylamine In ethanol for 1h; Reflux; Large scale; Stage #2: With hydrogenchloride In ethanol at 50 - 60℃; pH=2 - Ca. 3; Large scale;	90.3%

: 1372665-04-7
4-{4-[(5S)-5-((dibenzylamino)methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Stage #1: 4-{4-[(5S)-5-((dibenzylamino)methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one With palladium 10% on activated carbon; hydrogen In methanol at 40℃; for 6h; Stage #2: With hydrogenchloride In methanol for 4h; Reagent/catalyst;	90.2%

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

: 530-62-1
1,1'-carbonyldiimidazole

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Stage #1: 2-((2S)-2-hydroxy-3-{[4-(3-oxomorpholin-4-yl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione; 1,1'-carbonyldiimidazole With dmap In tetrahydrofuran for 12h; Reflux; Stage #2: With hydrogenchloride In water at 20℃; Concentration;	89.1%

: C18H23N3O6

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In ethanol at 55℃; for 2h;	85%

: 1403383-55-0
(S)-4-(4-((3-amino-2-hydroxypropyl)amino)phenyl)morpholin-3-one hydrochloride

: 530-62-1
1,1'-carbonyldiimidazole

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Stage #1: (S)-4-(4-((3-amino-2-hydroxypropyl)amino)phenyl)morpholin-3-one hydrochloride With potassium carbonate In 4-methyl-2-pentanone at 4℃; Inert atmosphere; Reflux; Stage #2: 1,1'-carbonyldiimidazole In 4-methyl-2-pentanone at 20℃; for 15h; Stage #3: With hydrogenchloride In water; 4-methyl-2-pentanone	80.1%

: 1403383-52-7
1-{(R)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxazolidin-5-ylmethyl}-3;5,7-triaza-1-azoniatricyclo[3.3.1.1(3,7)]decane iodide

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; water In ethanol at 50℃; for 2h; Inert atmosphere;	33.1%

: 1252018-10-2
4-[4-(N-(3-chloro-(2R)-2-hydroxy-1-propyl)amino)phenyl]morpholin-3-one

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: ammonia / water / 4 h / 20 °C 2.1: potassium carbonate / 4-methyl-2-pentanone / 4 °C / Inert atmosphere; Reflux 2.2: 15 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: acetonitrile / 3 h / 20 °C / Inert atmosphere 2: sodium iodide / sulfolane / 20 h / 110 °C 3: sulfolane / 72 h / 50 °C / Inert atmosphere 4: hydrogenchloride; water / ethanol / 2 h / 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 2 h / 100 °C 2: potassium carbonate / ethanol / 2 h / 60 °C 3: hydrogenchloride / ethanol / 2 h / 55 °C View Scheme
Multi-step reaction with 2 steps 1.1: methanol / 10 h / Reflux 2.1: dmap / tetrahydrofuran / 12 h / Reflux 2.2: 20 °C View Scheme

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

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium iodide / sulfolane / 20 h / 110 °C 2: sulfolane / 72 h / 50 °C / Inert atmosphere 3: hydrogenchloride; water / ethanol / 2 h / 50 °C / Inert atmosphere View Scheme

: 1252018-26-0
4-[4-((R)-5-(iodomethyl)-2-oxo-oxazolidin-3-yl)phenyl]-morpholin-3-one

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfolane / 72 h / 50 °C / Inert atmosphere 2: hydrogenchloride; water / ethanol / 2 h / 50 °C / Inert atmosphere View Scheme

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

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 4 h / Reflux 2.1: methylamine / ethanol; water / 2 h / 65 °C 2.2: 65 °C / pH 2.7 View Scheme
Multi-step reaction with 2 steps 1.1: potassium carbonate / dichloromethane / 5 h / 20 °C 2.1: methylamine / methanol / 6 h / 25 °C / Reflux 2.2: 1 h / 25 - 30 °C / pH 2 - 3 View Scheme
Multi-step reaction with 2 steps 1.1: dichloromethane / 8 h / 25 - 30 °C 2.1: methylamine / water; methanol / 5 h / 25 - 65 °C 2.2: 0.5 h / 25 - 30 °C / pH 1 - 2 View Scheme
Multi-step reaction with 2 steps 1.1: dmap / tetrahydrofuran / 25 h / Reflux; Large scale 2.1: ethanol / 1 h / Reflux; Large scale 2.2: 50 - 60 °C / pH 2 - Ca. 3 / Large scale View Scheme

: 438056-69-0
4-(4-aminophenyl)morpholin-3-one

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: ethanol / 9 h / 80 °C 2.1: tetrahydrofuran / 4 h / Reflux 3.1: methylamine / ethanol; water / 2 h / 65 °C 3.2: 65 °C / pH 2.7 View Scheme
Multi-step reaction with 3 steps 1.1: isopropyl alcohol; water / Reflux 2.1: potassium carbonate / dichloromethane / 5 h / 20 °C 3.1: methylamine / methanol / 6 h / 25 °C / Reflux 3.2: 1 h / 25 - 30 °C / pH 2 - 3 View Scheme
Multi-step reaction with 3 steps 1: ethanol / 24 h / Reflux 2: dichloromethane / 44 h / 20 °C 3: hydrogenchloride / methanol / 1 h / 20 °C View Scheme

: 1416129-92-4
tert-butyl {(5S)-3-[4-(3-oxo-4-morpholinyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methylcarbamate

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 20℃; for 1h;	26.5 g

: 1429333-95-8
tert-butyl N-[(R)-2-hydroxy-3-{4-(3-oxomorpholin-4-yl)phenylamino}propyl]carbamate

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 44 h / 20 °C 2: hydrogenchloride / methanol / 1 h / 20 °C View Scheme

: 1313613-18-1
[4-(3-oxo-morpholin-4-yl)phenyl]carbamic acid benzyl ester

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium tert-butoxide / N,N-dimethyl-formamide; methanol / 18 h / 0 - 25 °C 2: hydrogenchloride / methanol / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: lithium tert-butoxide / tetrahydrofuran / 48 h / 0 - 25 °C 2: hydrogenchloride / methanol / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: lithium tert-butoxide / N,N-dimethyl-formamide; tetrahydrofuran / 44 h / 20 °C / Cooling with ice 2: hydrogenchloride / methanol / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: lithium tert-butoxide; lithium chloride / tetrahydrofuran / 4 h / 50 °C / Inert atmosphere 2: hydrogenchloride / water / 0.75 h / 0 - 15 °C / pH 2 View Scheme

: 2-({2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
With methylamine In dichloromethane; water at 20 - 45℃; for 15h; Solvent;	58 g

: 586-78-7
para-nitrophenyl bromide

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: potassium carbonate / acetonitrile / 18 h / 60 °C 1.2: 2 h / 60 °C 2.1: iron; acetic acid / acetonitrile / 3 h / 30 °C 3.1: ethanol / 12 h / Reflux 4.1: N,N-dimethyl-formamide / 2 h / 100 °C 5.1: potassium carbonate / ethanol / 2 h / 60 °C 6.1: hydrogenchloride / ethanol / 2 h / 55 °C View Scheme

: 4-{4-[(5R)-5-(chloromethyl)-2-oxo-1,3-oxazole-3-yl]phenyl}morpholin-3-one

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / ethanol / 2 h / 60 °C 2: hydrogenchloride / ethanol / 2 h / 55 °C View Scheme

: 100-00-5
4-chlorobenzonitrile

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: potassium carbonate / acetonitrile / 6 h / 60 °C 1.2: 2 h / 60 °C 2.1: iron; acetic acid / acetonitrile / 3 h / 30 °C 3.1: ethanol / 12 h / Reflux 4.1: N,N-dimethyl-formamide / 2 h / 100 °C 5.1: potassium carbonate / ethanol / 2 h / 60 °C 6.1: hydrogenchloride / ethanol / 2 h / 55 °C View Scheme

: 446292-04-2
4-(4-nitrophenyl)-3-morpholinone

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: iron; acetic acid / acetonitrile / 3 h / 30 °C 2: ethanol / 12 h / Reflux 3: N,N-dimethyl-formamide / 2 h / 100 °C 4: potassium carbonate / ethanol / 2 h / 60 °C 5: hydrogenchloride / ethanol / 2 h / 55 °C View Scheme

: 350-46-9
4-Fluoronitrobenzene

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: potassium carbonate / acetonitrile / 18 h / 60 °C 1.2: 2 h / 60 °C 2.1: iron; acetic acid / acetonitrile / 3 h / 30 °C 3.1: ethanol / 12 h / Reflux 4.1: N,N-dimethyl-formamide / 2 h / 100 °C 5.1: potassium carbonate / ethanol / 2 h / 60 °C 6.1: hydrogenchloride / ethanol / 2 h / 55 °C View Scheme

: ethyl N-[4-(3-oxo-4-morpholinyl)phenyl]carbamate

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lithium tert-butoxide / dichloromethane / 0.5 h / 5 - 20 °C / Reflux; Large scale 1.2: 12 h / Large scale 2.1: hydrogenchloride / water; ethanol / 1.5 h / 20 °C / pH 2 - 3 / Large scale View Scheme

: 4-{4-[(R)-5-[(((4-chlorophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water at 20℃; for 1.5h; pH=2 - 3; Large scale;	1.45 kg

: 106-50-3
1,4-phenylenediamine

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: pyridine / tetrahydrofuran / 5 h / 10 - 20 °C 2.1: tetrabutylammomium bromide; potassium carbonate / dichloromethane / 5 h / 0 - 20 °C 3.1: isopropyl alcohol / 17 h / Reflux 4.1: methanol / 10 h / Reflux 5.1: dmap / tetrahydrofuran / 12 h / Reflux 5.2: 20 °C View Scheme

: N-(4-aminophenyl)-2-(2-chloroethoxy)acetamide

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: tetrabutylammomium bromide; potassium carbonate / dichloromethane / 5 h / 0 - 20 °C 2.1: isopropyl alcohol / 17 h / Reflux 3.1: methanol / 10 h / Reflux 4.1: dmap / tetrahydrofuran / 12 h / Reflux 4.2: 20 °C View Scheme

: 4-[4-(methylideneamino)phenyl]morpholin-3-one

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 7 h / 0 - 5 °C 2.1: methylamine / ethanol; water / 8 h / 40 - 60 °C 2.2: 2 h / 15 °C View Scheme
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 7 h / 0 - 5 °C 2.1: methylamine / ethanol; water / 8 h / 40 - 60 °C 2.2: 15 °C / pH 1 - 2 View Scheme

: 1252018-07-7
methyl N-[4-(3-oxo-4-morpholinyl)phenyl]carbamate

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium chloride; lithium hexamethyldisilazane / tetrahydrofuran / 12 h / 30 °C / Inert atmosphere 2: hydrogenchloride / water / 0.75 h / 0 - 15 °C / pH 2 View Scheme

: 106-40-1
4-bromo-aniline

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: copper(l) iodide; N,N`-dimethylethylenediamine; potassium carbonate / toluene / Inert atmosphere 2: sodium hydrogencarbonate / dichloromethane / 4 h / 25 °C 3: lithium tert-butoxide; lithium chloride / tetrahydrofuran / 4 h / 50 °C / Inert atmosphere 4: hydrogenchloride / water / 0.75 h / 0 - 15 °C / pH 2 View Scheme

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

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

Conditions

Conditions	Yield
In dichloromethane; water pH=8; Concentration;	96.7%
With potassium carbonate In methanol at 25 - 30℃; for 0.5h;	56%
With potassium carbonate In methanol at 25 - 30℃; for 0.5h;	56%
With potassium carbonate In water at 20℃; for 2h;

: 24065-33-6
5-Chlorothiophene-2-carboxylic acid

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
Stage #1: 5-Chlorothiophene-2-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 25℃; for 0.5h; Stage #2: 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidine-3-yl]phenyl}morpholin-3-one hydrochloride In N,N-dimethyl-formamide at 34℃; for 4h;	96.3%
With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In N,N-dimethyl-formamide at 20℃; for 2.83333h; Reagent/catalyst; Cooling with ice;	95.2%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 24h; pH=8 - 9; Large scale;	94.7%

: 89166-94-9
5-chlorothiophene-2-carboxylic acid chloride

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
With triethylamine In water; acetone; toluene at 30 - 35℃; for 2h; Temperature; Concentration;	93.3%

: 42518-98-9
5-chlorothiophene-2-carbonyl chloride

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
With sodium carbonate In water; acetone; toluene at 8 - 53℃;	93.12%
With sodium carbonate In water; acetone; toluene at 10 - 53℃; for 0.5h; High pressure;	90%
With potassium carbonate In dichloromethane at 25 - 30℃; for 5h;	88%

: 42518-98-9
5-chlorothiophene-2-carbonyl chloride

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

: 482306-32-1
5-chloro-N-({(5)-2-oxo-3-[4-(3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidin-5-yl}-methyl)-2-thiophenecarboxamide

Conditions

Conditions	Yield
With potassium carbonate In acetone for 2h; Heating;	85%

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

: 1450877-56-1
4-nitrophenyl 5-chlorothiophene-2-carboxylate

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 35 - 40℃; Reagent/catalyst; Solvent; Temperature;	82.7%
With triethylamine In dimethyl sulfoxide; acetonitrile at 35 - 40℃;	82.7%

: 89283-13-6
4,5-dichlorothiophene-2-carbonyl chloride

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

: (S)-4,5-dichloro-N-[[2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl]methyl]-2-thiophenecarboxamide

Conditions

Conditions	Yield
With sodium carbonate In water; acetone at 20℃;	82.1%
With sodium carbonate In water; toluene at 8 - 20℃; for 2h;

: 64-18-6
formic acid

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

: 1616563-62-2
N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)formamide

Conditions

Conditions	Yield
Stage #1: 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidine-3-yl]phenyl}morpholin-3-one hydrochloride With ammonia In dichloromethane for 0.25h; Stage #2: formic acid In water; toluene at 110 - 120℃;	80%

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

: 350-46-9
4-Fluoronitrobenzene

: (S)-4-(4-(5-(((4-nitrophenyl)amino)methyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one

Conditions

Conditions	Yield
With potassium carbonate In ethyl acetate for 24h; Reflux;	75.4%

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

: 1151893-81-0
2-{2-[1-(5-chlorothiophen-2-yl)-N-{4-[(5S)-5-{[(5-chlorothiophen-2-yl)formamido]methyl}-2-oxo-1,3-oxazolidin-3-yl]phenyl}formamido]ethoxy}acetic acid

: 5-chloro-N-(4-((S)-5-((5-chlorothiophene-2-carboxamido)methyl)-2-oxooxazolidin-3-yl)phenyl)-N-(2-(2-oxo-2-((((S)-2-oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)amino)ethoxy)ethyl)thiophene-2-carboxamide

Conditions

Conditions	Yield
Stage #1: 2-{2-[1-(5-chlorothiophen-2-yl)-N-{4-[(5S)-5-{[(5-chlorothiophen-2-yl)formamido]methyl}-2-oxo-1,3-oxazolidin-3-yl]phenyl}formamido]ethoxy}acetic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 0 - 20℃; Cooling with ice; Stage #2: With triethylamine In N,N-dimethyl-formamide at 10 - 20℃; Stage #3: 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidine-3-yl]phenyl}morpholin-3-one hydrochloride In N,N-dimethyl-formamide at 30 - 35℃;	48.6%
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 10h; Inert atmosphere;	42.6%

Yield

Stage #1: 2-{2-[1-(5-chlorothiophen-2-yl)-N-{4-[(5S)-5-{[(5-chlorothiophen-2-yl)formamido]methyl}-2-oxo-1,3-oxazolidin-3-yl]phenyl}formamido]ethoxy}acetic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 0 - 20℃; Cooling with ice;
Stage #2: With triethylamine In N,N-dimethyl-formamide at 10 - 20℃;
Stage #3: 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidine-3-yl]phenyl}morpholin-3-one hydrochloride In N,N-dimethyl-formamide at 30 - 35℃;

48.6%

With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 10h; Inert atmosphere;

42.6%

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

: 32315-10-9
bis(trichloromethyl) carbonate

: C29H32N6O9

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 4h;	14%

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

: 32315-10-9
bis(trichloromethyl) carbonate

: 1365267-35-1
N,N'-bis[{(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl]urea

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃;	13.1%

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

: 86427-02-3
3-chlorothiophene-2-carbonyl chloride

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
Stage #1: 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidine-3-yl]phenyl}morpholin-3-one hydrochloride With triethylamine In 1-methyl-pyrrolidin-2-one for 0.25h; Stage #2: 3-chlorothiophene-2-carbonyl chloride In 1-methyl-pyrrolidin-2-one at 10 - 82℃;

: 35475-03-7
methyl 5-chloro-2-thiophenecarboxylate

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
at 120℃; for 48h; Product distribution / selectivity; Inert atmosphere; Heating;

4-[4-[(5S)-5-(Aminomethyl)-2-oxo-3-oxazolidinyl]phenyl]-3-morpholinone hydrochloride Specification

The 4-[4-[(5S)-5-(Aminomethyl)-2-oxo-3-oxazolidinyl]phenyl]-3-morpholinone hydrochloride, with the CAS registry number 898543-06-1, is also known as (S)-4-(4-(5-(Aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one hydrochloride. It belongs to the product category of Intermediates. This chemical's molecular formula is C₁₄H₁₇N₃O₄^.HCl and molecular weight is 327.77. What's more, its systematic name is 4-{4-[(5S)-5-(Aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}-3-morpholinone hydrochloride (1:1).

Physical properties of 4-[4-[(5S)-5-(Aminomethyl)-2-oxo-3-oxazolidinyl]phenyl]-3-morpholinone hydrochloride are: (1)ACD/BCF (pH 5.5): 1.00; (2)ACD/BCF (pH 7.4): 1.00; (3)ACD/KOC (pH 5.5): 1.00; (4)ACD/KOC (pH 7.4): 1.00; (5)#H bond acceptors: 7; (6)#H bond donors: 2; (7)#Freely Rotating Bonds: 4; (8)Polar Surface Area: 62.32 Å²; (9)Flash Point: 313 °C; (10)Enthalpy of Vaporization: 90.17 kJ/mol; (11)Boiling Point: 593.9 °C at 760 mmHg; (12)Vapour Pressure: 2.18E-14 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Cl.O=C1O[C@@H](CN)CN1c3ccc(N2C(=O)COCC2)cc3
(2)Std. InChI: InChI=1S/C14H17N3O4.ClH/c15-7-12-8-17(14(19)21-12)11-3-1-10(2-4-11)16-5-6-20-9-13(16)18;/h1-4,12H,5-9,15H2;1H/t12-;/m0./s1
(3)Std. InChIKey: ITMQDYQHNKXERQ-YDALLXLXSA-N

Product Name

(S)-4-(4-(5-(Aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one.HCl

Synthetic route

4-[4-[(5S)-5-(Aminomethyl)-2-oxo-3-oxazolidinyl]phenyl]-3-morpholinone hydrochloride Specification

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