4319-49-7

Basic information

• Product Name: N-Aminomorpholine
• Synonyms: Morpholine, 4-amino-;morpholin-4-ylamine;4-Aminomorpholine,98%;4-Aminomorpholine>97%;4-Morpholinamine(9CI);4-AMINOMORPHOLINE 97+%;4-Aminomonpholine;N-Aminomorpholine,97%
• CAS NO: 4319-49-7
• Molecular Formula: C₄H₁₀N₂O
• Molecular Weight: 102.14
• EINECS: 224-347-4
• Product Categories: VARIOUSAMINE;Aromatic Morpholines;Amines;Morpholines & Thiomorpholines;Morpholines & Thiomorpholines;Building Blocks;Heterocyclic Building Blocks;Morpholines
• Mol File: 4319-49-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 168 °C(lit.)
• Flash Point: 137 °F
• Appearance: Clear colorless to faintly yellow/Liquid
• Density: 1.059 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.65mmHg at 25°C
• Refractive Index: n20/D 1.4772(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform, Methanol (Slightly)
• PKA: pK1: 4.19(+1) (25°C)
• Water Solubility: miscible
• Sensitive: Air Sensitive
• CAS DataBase Reference: N-Aminomorpholine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Aminomorpholine(4319-49-7)
• EPA Substance Registry System: N-Aminomorpholine(4319-49-7)

Safety Data

• Hazard Codes: Xn,F,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-23-16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: QD7300000
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 4319-49-7(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to faintly yellow liquid

Uses

4-Aminomorpholine can be used to prepare antiviral agents to prevent and treat influenza.

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 3470, 1984 DOI: 10.1021/jo00193a007

InChI:InChI=1/C4H12N2O/c5-6-1-3-7-4-2-6/h6H,1-4H2,5H3/q+2

Synthetic route

N-nitrosomorpholine (59-89-2) → 1-aminomorpholine (4319-49-7)

Conditions	Yield
With titanium(III) chloride In water for 1h; Ambient temperature;	76%
With ethanol; sodium
With zinc In acetic acid

N-nitrosomorpholine (59-89-2) → 1-aminomorpholine (4319-49-7) + N,N'-bis(morpholino)diazene (57902-11-1)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 0 - 10℃; for 3h; 1) R.T., 1 h 2) reflux, 3 h;	A 31% B 1.0 g
With lithium aluminium tetrahydride In diethyl ether at 0 - 10℃; for 3h; 1) R.T., 1 h 2) reflux, 3 h;	A 31% B 31%

morpholine (110-91-8) → 1-aminomorpholine (4319-49-7)

Conditions	Yield
With chloroamine
With potassium hydroxide; hydroxylamine-O-sulfonic acid In water for 0.166667h; Heating;
With ammonium acetate; hydrogenchloride; sodium nitrite In methanol; water

N,N-di(2-hydroxyethyl)hydrazine (13529-51-6) → morpholine (110-91-8) + 1-aminomorpholine (4319-49-7)

Conditions	Yield
With sulfuric acid

3-oxa-1,5-dichloropentane (111-44-4) → 1-aminomorpholine (4319-49-7)

Conditions	Yield
With ethanol; hydrazine hydrate

N-nitrosomorpholine (59-89-2) → morpholine (110-91-8) + 1-aminomorpholine (4319-49-7)

Conditions	Yield
With titanium(III) chloride; ammonium acetate In water for 1h; Product distribution; Ambient temperature; variation of reaction conditions ( pH<1, pH=9.4 );	A 3 % Chromat. B 86 % Chromat.
With hydrogenchloride; zinc In water for 24h; Product distribution; Ambient temperature;	A 8 % Chromat. B 98 % Chromat.
With potassium hydroxide; aluminium In water for 24h; Product distribution; Ambient temperature;	A 43 % Chromat. B 64 % Chromat.

N-nitromorpholine (4164-32-3) → morpholine (110-91-8) + 1-aminomorpholine (4319-49-7)

Conditions	Yield
With acetic acid In acetonitrile Product distribution; Mechanism;

N-nitrosomorpholine (59-89-2) → 1-aminomorpholine (4319-49-7) + dimorpholino-diimide

Conditions	Yield
With acetic acid; zinc

N-nitrosomorpholine (59-89-2) + acetic acid (64-19-7) + zinc dust → 1-aminomorpholine (4319-49-7) + dimorpholino-diimide

ethanol (64-17-5) + hydrazine hydrate (7803-57-8) + 3-oxa-1,5-dichloropentane (111-44-4) → 1-aminomorpholine (4319-49-7)

water (7732-18-5) + hydrazine hydrate (7803-57-8) + 3-oxa-1,5-dichloropentane (111-44-4) → 1-aminomorpholine (4319-49-7) + 4,4'-bimorpholine (17173-82-9) + bis-(2-morpholinoamino-ethyl)-ether

Ni(H2NC6H4SO2NC3H2NS)2(4-amino-morpholine)2 → 1-aminomorpholine (4319-49-7) + sulfanilic acid thiazol-2-ylamide; nickel (II)-salt

Conditions	Yield
With H2O or aq. mineral acid decompn. with H2O or dild. aq. mineral acid;
decompn. on heating;
decompn. on heating;
With H2O or aq. mineral acid decompn. with H2O or dild. aq. mineral acid;

O(CH2CH2)2NNH2*BH3 (21223-18-7) + water (7732-18-5) → 1-aminomorpholine (4319-49-7) + hydrogen (1333-74-0) + boric acid (11113-50-1)

Conditions	Yield
In water
In water

1-aminomorpholine (4319-49-7) + p-toluenesulfonyl chloride (98-59-9) → 4-methyl-N-morpholin-4-ylbenzenesulfonamide (351186-41-9)

Conditions	Yield
With triethylamine In dichloromethane at 4℃;	100%
In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	17 mg

1-aminomorpholine (4319-49-7) + 1-(2,4-dichlorophenyl)-6-methyl-1H-benzofuro[3,2-0c]pyrazole-3-carboxylic acid (1240998-70-2) → N-(morpholin-1-yl)-1-(2,4-dichlorophenyl)-6-methyl-1H-benzofuro[3,2-c]pyrazole-3-carbohydrazide (1240996-83-1)

Conditions	Yield
Stage #1: 1-(2,4-dichlorophenyl)-6-methyl-1H-benzofuro[3,2-0c]pyrazole-3-carboxylic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 1h; Stage #2: 1-aminomorpholine In dichloromethane at 20℃; for 22h;	100%

1-aminomorpholine (4319-49-7) + formaldehyd (50-00-0) + 7-[4-(4-{[(4-benzyl-5-mercapto-4H-1,2,4-triazole-3-yl)methyl]amino}-2-fluorophenyl)piperazin-1-yl]-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-carboxylic acid → 7-(4-{4-[({4-benzyl-1-[(morpholin-4-ylamino)methyl]-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl}methyl)amino]-2-fluorophenyl}piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 0.1h; Temperature; Reagent/catalyst; Solvent; Mannich Aminomethylation; Microwave irradiation;	100%

1-aminomorpholine (4319-49-7) + 5-ethylfurfural (23074-10-4) → [1-(5-Ethyl-furan-2-yl)-meth-(E)-ylidene]-morpholin-4-yl-amine (125142-80-5)

Conditions	Yield
In ethanol for 0.5h; heating on a steam bath;	99%

1-aminomorpholine (4319-49-7) + 4-methoxyphenylboronic acid (5720-07-0) → 4-methoxy-N-morpholinobenzenesulfonamide (557780-43-5)

Conditions	Yield
With DABCO-bis(sulfur dioxide); tetrabutylammomium bromide; oxygen; palladium diacetate In 1,4-dioxane at 80℃; for 12h;	99%

1-aminomorpholine (4319-49-7) + diethoxydiphenylsilane (2553-19-7) → N‐morpholinobenzenesulfonamide (351186-42-0)

Conditions	Yield
With 1,4-diazabicyclo[2.2.2]octane-triethylenediamine-bis(sulfur dioxide); oxygen; copper diacetate; cesium fluoride; XPhos In 1,4-dioxane at 80℃;	99%

1-aminomorpholine (4319-49-7) + C9H8ClN2O(1+)*BF4(1-) → 1-(6-chloro-2,3-dihydrobenzofuran-3-yl)-N-morpholinomethanesulfonamide

Conditions	Yield
With 1,4-diazabicyclo[2.2.2]octane-triethylenediamine-bis(sulfur dioxide) In acetonitrile at 25℃; for 0.166667h; Inert atmosphere;	99%

1-aminomorpholine (4319-49-7) + Methyl 3-formylbenzoate (52178-50-4) → (E)-methyl 3-((morpholinoimino)methyl)benzoate

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃; for 22h; Inert atmosphere;	99%
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere;

1-aminomorpholine (4319-49-7) + 2-methylphenyl aldehyde (529-20-4) → (E)-N-(2-methylbenzylidene)morpholin-4-amine

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃; for 24h; Inert atmosphere;	99%
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;	94%
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere;

1-aminomorpholine (4319-49-7) + 4-Trifluoromethylbenzaldehyde (455-19-6) → (E)-N-morpholino-1-(4-(trifluoromethyl)phenyl)methanimine

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃; for 18h; Inert atmosphere;	99%
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;	92%
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere;	92%
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere;

1-aminomorpholine (4319-49-7) + formaldehyd (50-00-0) + 1-ethyl-6-fluoro-4-oxo-7-{4-[(5-oxo-4-phenyl-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl] piperazin-1-yl}-1,4-dihydroquinoline-3-carboxylic acid → 1-ethyl-6-fluoro-7-{4-{[1-[(morpholin-4-ylamino)methyl]-5-oxo-4-phenyl-4,5-dihydro-1H-1,2,4-triazol-3-yl]methyl}piperazin-1-yl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions	Yield
With hydrogenchloride for 0.116667h; Time; Microwave irradiation;	99%

1-aminomorpholine (4319-49-7) + 2-Fluorobenzaldehyde (446-52-6) → (E)-1-(2-fluorophenyl)-N-morpholinomethanimine

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃; for 16h; Inert atmosphere;	99%

1-aminomorpholine (4319-49-7) + diethyl 2-ethoxymethylenemalonate (87-13-8) → (morpholinyl-4 amino)-3 ethoxycarbonyl-2 propenoate d'ethyle (94621-02-0)

Conditions	Yield
In methanol for 1h; Ambient temperature;	98%

1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methyl-1H-imidazole-4-carboxylic acid (796875-26-8) + 1-aminomorpholine (4319-49-7) → 1-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-5-methyl-N-(morpholin-4-yl)-1H-imidazole-4-carboxamide

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 16h;	98%

1-aminomorpholine (4319-49-7) + 2-Methylphenylboronic acid (16419-60-6) → 2-methyl-N-morpholinobenzenesulfonamide (1255365-30-0)

Conditions	Yield
With DABCO-bis(sulfur dioxide); tetrabutylammomium bromide; oxygen; palladium diacetate In 1,4-dioxane at 80℃; for 12h;	98%

1-aminomorpholine (4319-49-7) + phenylboronic acid (98-80-6) → N‐morpholinobenzenesulfonamide (351186-42-0)

Conditions	Yield
With DABCO-bis(sulfur dioxide); tetrabutylammomium bromide; oxygen; palladium diacetate In 1,4-dioxane at 80℃; for 12h;	98%

1-aminomorpholine (4319-49-7) + 3,3-diethyl-1-(4-methylphenyl)-1-triazene (36719-51-4) → 4-methyl-N-morpholin-4-ylbenzenesulfonamide (351186-41-9)

Conditions	Yield
With boron trifluoride diethyl etherate; sulfur dioxide In acetonitrile at 60℃; for 3h; Inert atmosphere; Schlenk technique;	98%

1-aminomorpholine (4319-49-7) + 4-fluorobenzaldehyde (459-57-4) → (E)-1-(4-fluorophenyl)-N-morpholinomethanimine

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;	98%
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere;	93%
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere;

1-aminomorpholine (4319-49-7) + 4-cyanobenzaldehyde (105-07-7) → (E)-4-((morpholinoimino)methyl)benzonitrile

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃; for 20h; Inert atmosphere;	98%
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;	83%
With magnesium sulfate In dichloromethane at 20℃;

1-aminomorpholine (4319-49-7) + carbon disulfide (75-15-0) + 3-chloroprop-1-ene (107-05-1) → 2-(morpholine-4-yl)imino-4-(iodomethyl)-1,3-dithiolane

Conditions	Yield
Stage #1: 1-aminomorpholine; carbon disulfide; 3-chloroprop-1-ene With potassium carbonate In neat liquid at 0 - 20℃; Green chemistry; Stage #2: With iodine In neat liquid at 20℃; for 0.3h; Green chemistry;	98%

Upstream product

• 13529-51-6 N,N-di(2-hydroxyethyl)hydrazine 
• 21223-18-7 O(CH₂CH₂)2NNH₂*BH₃ 
• 7732-18-5 water 
• 7803-57-8 hydrazine hydrate 
• 111-44-4 3-oxa-1,5-dichloropentane 
• 64-17-5 ethanol 
• 59-89-2 N-nitrosomorpholine 
• 64-19-7 acetic acid 
• 4164-32-3 N-nitromorpholine 
• 110-91-8 morpholine 

Downstream Products

• 117911-77-0 4-(Morpholin-4-ylamino)-benzonitrile 

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