622-40-2

Basic information

• Product Name: 2-Morpholinoethanol
• Synonyms: 2-(morpholinyl)-ethano;2-morpholino-ethano;beta-Morpholinoethanol;beta-Oxyaethyl-morpholin;Ethanol, 2-(morpholinyl)-;Ethanol, 2-morpholino-;hydroxyethylmorpholine;N-(2-Hydroxyethyl)morfolin
• CAS NO: 622-40-2
• Molecular Formula: C₆H₁₃NO₂
• Molecular Weight: 131.17
• EINECS: 210-734-5
• Product Categories: Building Blocks;C4 to C10;Chemical Synthesis;Heterocyclic Building Blocks;Morpholines/Thiomorpholines
• Mol File: 622-40-2.mol
• Article Data: 35

Chemical Properties

• Melting Point: -1 °C
• Boiling Point: 227 °C757 mm Hg(lit.)
• Flash Point: 211 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.083 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0183mmHg at 25°C
• Refractive Index: n20/D 1.476(lit.)
• Storage Temp.: 2-8°C
• PKA: 14.88±0.10(Predicted)
• Explosive Limit: 1.5-9.8%(V)
• Water Solubility: miscible
• BRN: 104375
• CAS DataBase Reference: 2-Morpholinoethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Morpholinoethanol(622-40-2)
• EPA Substance Registry System: 2-Morpholinoethanol(622-40-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 1
• RTECS: QE3510000
• F: 10-23
• TSCA: Yes
• Hazardous Substances Data: 622-40-2(Hazardous Substances Data)

Usage

Chemical Properties

2-Morpholinoethanol is a transparent colorless to yellow liquid. It is used as an organic chemical synthesis intermediate.

Uses

4-(2-Hydroxyethyl)morpholine is a morphiline derivative used in the preparation of ester prodrugs of naproxen. 4-(2-Hydroxyethyl)morpholine was also shown to induce repair in rat hepatocyte primary cu lture/DNA.

Definition

ChEBI: 2-Morpholinoethanol is a primary alcohol that is ethanol in which one of the methyl hydrogens is replaced by a morpholin-4-yl group. It is a primary alcohol, a tertiary amino compound and a member of morpholines.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C4H9NO.C2H6O/c1-3-6-4-2-5-1;1-2-3/h5H,1-4H2;3H,2H2,1H3

Synthetic route

morpholine (110-91-8) + ethylene glycol (107-21-1) → 2-(morpholin-4-yl)ethanol (622-40-2)

Conditions	Yield
With triphenylphosphine; ruthenium trichloride at 120℃; for 2h;	100%

morpholine (110-91-8) + 2-bromoethanol (540-51-2) → 2-(morpholin-4-yl)ethanol (622-40-2)

Conditions	Yield
at 80℃; for 72h;	85%
With potassium carbonate In acetonitrile for 3h; Reflux;	83%
With potassium carbonate In acetonitrile for 3h; Reflux;	83%

ethanolamine (141-43-5) + 3-oxa-1,5-dichloropentane (111-44-4) → 2-(morpholin-4-yl)ethanol (622-40-2)

Conditions	Yield
With sodium carbonate In acetonitrile for 48h; Heating;	83%
at 90 - 170℃;
With potassium carbonate at 120℃;
With ethanol; copper

N-morpholylacetic acid ethyl ester (3235-82-3) → 2-(morpholin-4-yl)ethanol (622-40-2)

Conditions	Yield
With sodium tetrahydroborate In methanol at 0 - 50℃; for 8h;	76.6%

morpholine (110-91-8) + 2-chloro-ethanol (107-07-3) → 2-(morpholin-4-yl)ethanol (622-40-2)

Conditions	Yield
With sodium hydroxide at 40 - 45℃;	67%
With acetone
With benzene

oxirane (75-21-8) + morpholine (110-91-8) → 2-(morpholin-4-yl)ethanol (622-40-2)

Conditions	Yield
With water at 0℃;
With methanol

triethanolamine (102-71-6) → 2-(morpholin-4-yl)ethanol (622-40-2)

Conditions	Yield
With sulfuric acid at 160 - 170℃;
With cation exchanger at 160 - 220℃;
With sulfuric acid at 130 - 150℃; for 15h;

triethanolamine hydrochloride (637-39-8) → morpholine (110-91-8) + 2-(morpholin-4-yl)ethanol (622-40-2) + 1,2-dimorpholylethane (1723-94-0) + 2,2'-dimorpholinodiethyl ether (6425-39-4)

Conditions	Yield
at 190 - 230℃;

triethanolamine hydrochloride (637-39-8) → 2-(morpholin-4-yl)ethanol (622-40-2)

Conditions	Yield
at 200 - 205℃; under 40 Torr; anschliessend Erhitzen mit wss.-aethanol. KOH;
at 200 - 205℃; under 40 Torr;
at 280℃; under 7 Torr; anschliessend Erhitzen mit wss.-aethanol. KOH;

3-oxa-1,5-dichloropentane (111-44-4) → 2-(morpholin-4-yl)ethanol (622-40-2)

Conditions	Yield
With ammonium hydroxide at 65 - 80℃; under 2206.5 - 3677.5 Torr; anschliessend Behandeln mit wss. NaOH;

morpholine (110-91-8) + ethylene glycol (107-21-1) → 2-(morpholin-4-yl)ethanol (622-40-2) + 1,2-dimorpholylethane (1723-94-0)

Conditions	Yield
With triphenylphosphine; ruthenium trichloride at 120℃; for 2h; Product distribution; other catalyst, also with THF, other phosphine, also at 220 degC;
With hydridochlorotris(triphenylphosphine)ruthenium(II) at 100℃; for 5.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With ruthenium trichloride at 120℃; for 2.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With Ru(CO)12; triphenylphosphine In tetrahydrofuran at 220℃; for 15h; Yield given;
With tris(triphenylphosphine)ruthenium(II) chloride at 100℃; for 2h; Product distribution; Mechanism; other diol; other secondary amines; other catalysts; var. temp. and reaction times;

methyl 2-morpholin-4-ylacetate (35855-10-8) → 2-(morpholin-4-yl)ethanol (622-40-2)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran Heating;

ethanolamine (141-43-5) + diethylene glycol ditosylate (7460-82-4) → 2-(morpholin-4-yl)ethanol (622-40-2)

phenyl-carbamic acid-(2-morpholino-ethyl ester); hydrochloride (50594-07-5) → 2-(morpholin-4-yl)ethanol (622-40-2) + carbon dioxide (124-38-9) + aniline (62-53-3)

Conditions	Yield
With sodium hydroxide In ethanol; water at 40℃; Rate constant; Thermodynamic data; var. temp., EA;

2,2'-diiodoethyl ether (34270-90-1) + ammonia (7664-41-7) → 2-(morpholin-4-yl)ethanol (622-40-2)

tris-(2-chloro-ethyl)-amine (555-77-1) + aqueous Na2CO3 → 2-(morpholin-4-yl)ethanol (622-40-2)

tris-(2-chloro-ethyl)-amine (555-77-1) + KOH <0.05n> → 2-(morpholin-4-yl)ethanol (622-40-2)

morpholine (110-91-8) + Iodoethanol (624-76-0) → 2-(morpholin-4-yl)ethanol (622-40-2)

Conditions	Yield
With potassium carbonate; sodium iodide In ethanol for 12h; Reflux;

triethanolamine (102-71-6) + ethanolamine (141-43-5) → 2-(morpholin-4-yl)ethanol (622-40-2) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With oxygen; zirconium(IV) oxide In water at 325℃; under 760.051 Torr; Product distribution / selectivity;

1,2-dimorpholinoethane-1,2-dione (6342-79-6) → 2-(morpholin-4-yl)ethanol (622-40-2) + 2-hydroxy-1-(morpholin-4-yl)ethan-1-one (51068-78-1) + ethylene glycol (107-21-1)

Conditions	Yield
With hydrogen; Cu/Al2O3/SiO2 In methanol at 170℃; under 41254.1 Torr; for 16.5h; Autoclave;

triethanolamine (102-71-6) → 2-(morpholin-4-yl)ethanol (622-40-2) + 2,2'-dimorpholinodiethyl ether (6425-39-4)

Conditions	Yield
With sulfuric acid at 130 - 200℃; for 15h; Temperature; Time;

2-(morpholin-4-yl)ethanol (622-40-2) → N-(2-bromoethyl)morpholine (89583-07-3)

Conditions	Yield
With dibromotriphenylphosphorane In dichloromethane at 0 - 20℃;	100%
With phosphorus tribromide In dichloromethane at 0 - 45℃;	23.7%
With hydrogen bromide at 130℃;

2-(morpholin-4-yl)ethanol (622-40-2) → 4-(2-hydroxyethyl)morpholine 4-oxide (95925-60-3)

Conditions	Yield
With dihydrogen peroxide	100%

2-(morpholin-4-yl)ethanol (622-40-2) + 4-fluoro-2-methoxy-1-nitrobenzene (448-19-1) → 4-(2-(3-methoxy-4-nitrophenoxy)ethyl)morpholine (342435-24-9)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide In water; toluene at 18 - 60℃; for 22h;	100%
With tetrabutylammomium bromide; water; potassium hydroxide In toluene at 60℃; for 18h;	98%
With benzyltriethylammonium bromide; potassium hydroxide In water; toluene at 60℃; for 24h;	42.4%
With tetrabutyl-ammonium chloride; potassium hydroxide In toluene at 60℃; for 24h;	42%

2-(morpholin-4-yl)ethanol (622-40-2) + 4-bromo-phenol (106-41-2) → 1-bromo-4-(2-morpholinoethoxy)benzene (836-59-9)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 110℃; for 17h; Mitsunobu Displacement; Inert atmosphere;	100%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 2.16667h;

2-(morpholin-4-yl)ethanol (622-40-2) + ethyl 1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylate (851728-86-4) → 1-(2-chlorophenyl)-5-(4-chlorophenyl)-3-ethoxycarbonyl-4-(2-morpholinoethoxy)-1H-pyrazole (935259-86-2)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;	100%

2-(morpholin-4-yl)ethanol (622-40-2) + 3-chlorosulfonyl-4-chlorobenzoyl chloride (62574-66-7) → 2-(morpholin-4-yl)ethyl 4-chloro-3-chlorosulfonylbenzoate (1135370-76-1)

Conditions	Yield
In dichloromethane for 12h;	100%

2-(morpholin-4-yl)ethanol (622-40-2) → 2-morpholin-4-yl-potassium ethoxide (1169860-18-7)

Conditions	Yield
With potassium In ethanol at 0℃; Product distribution / selectivity;	100%

2-(morpholin-4-yl)ethanol (622-40-2) + 8-bromo-1-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-(4-chlorobenzyl)-3-methyl-1H-purine-2,6(3H,7H)-dione → 1-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-(4-chlorobenzyl)-3-methyl-8-(2-morpholinoethoxy)-1H-purine-2,6(3H,7H)-dione

Conditions	Yield
With sodium at 20℃; for 24h;	100%

2-(morpholin-4-yl)ethanol (622-40-2) + 1,2-dichloro-4-fluoro-5-nitrobenzene (2339-78-8) → 4-[2-(4,5-dichloro-2-nitrophenoxy)ethyl]morpholine

Conditions	Yield
Stage #1: 2-(morpholin-4-yl)ethanol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.166667h; Stage #2: 1,2-dichloro-4-fluoro-5-nitrobenzene In tetrahydrofuran; mineral oil at 0℃; for 1h;	100%

2-(morpholin-4-yl)ethanol (622-40-2) + C24H29BrIN5O4 → C25H33BrN6O4

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate at 110℃; for 0.5h; Microwave irradiation;	100%

2-(morpholin-4-yl)ethanol (622-40-2) + 4-benzyloxy-2-fluoro-1-nitrobenzene (221040-07-9) → 4-{2-[5-(benzyloxy)-2-nitrophenoxy]ethyl}morpholine

Conditions	Yield
Stage #1: 2-(morpholin-4-yl)ethanol With sodium hydride In tetrahydrofuran; mineral oil at 20 - 30℃; for 1h; Stage #2: 4-benzyloxy-2-fluoro-1-nitrobenzene In tetrahydrofuran; mineral oil at 20℃; for 1h;	99.2%

2-(morpholin-4-yl)ethanol (622-40-2) → 3,3-diphenylpropyl 4-(2-(1-morpholine)ethoxy)acetoacetate

Conditions	Yield
	99%

2-(morpholin-4-yl)ethanol (622-40-2) + 6-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid isopropyl amide → 6-(2-morpholine-4-ylethoxy)-1-oxo-3-phenyl-1H-indene-2-carboxylic acid isopropyl amide (867187-72-2)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; benzene at 0 - 20℃; for 2h;	99%

2-(morpholin-4-yl)ethanol (622-40-2) + ethyl 2-oxocyclohexane carboxylate (1655-07-8) → C13H21NO4

Conditions	Yield
In toluene for 120h; Reflux;	98%

2-(morpholin-4-yl)ethanol (622-40-2) + 6-chloropyridine-3-ol (41288-96-4) → 4-(2-((6-chloropyridin-3-yl)oxy)ethyl)morpholine (879487-97-5)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 4h;	97%

2-(morpholin-4-yl)ethanol (622-40-2) + 1-bromomethyl-4-iodobenzene (16004-15-2) → 4-(2-hydroxyethyl)-4-(4-iodobenzyl)morpholin-4-ium bromide

Conditions	Yield
at 72℃; for 18h;	97%
In N,N-dimethyl-formamide at 72℃; Inert atmosphere;	97%

2-(morpholin-4-yl)ethanol (622-40-2) + 1,3-Benzothiazole (95-16-9) + 2-amino-6-hydroxybenzothiazole (26278-79-5) + diethylazodicarboxylate (1972-28-7) → 6-(2-morpholinoethoxy)benzo[d]thiazol-2-amine

Conditions	Yield
With sodium hydrogencarbonate; triphenylphosphine In tetrahydrofuran; ethyl acetate	96%
With sodium hydrogencarbonate; triphenylphosphine In tetrahydrofuran; ethyl acetate	96%
With sodium hydrogencarbonate; triphenylphosphine In tetrahydrofuran; ethyl acetate	96%

2-(morpholin-4-yl)ethanol (622-40-2) + 2-Fluoro-5-nitrobenzotrifluoride (400-74-8) → 4-[2-(4-nitro-2-trifluoromethyl-phenoxy)-ethyl]-morpholine (850797-92-1)

Conditions	Yield
Stage #1: 2-(morpholin-4-yl)ethanol With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2-Fluoro-5-nitrobenzotrifluoride In tetrahydrofuran at 20℃; for 4h;	96%

2-(morpholin-4-yl)ethanol (622-40-2) + 8,8′,8″-(hydroxymethanetriyl)tris[2,2,6,6-tetramethylbenzo[1,2-d:4,5-d′]bis([1,3]dithiole)-4-carboxylic acid] (910912-09-3) → tris(2,2,6,6-tetramethyl-8-{[2-(morpholin-4-yl)ethyl]carbonyl}-benzo[1,2-d;4,5-d']bis[1,3]dithiol-4-yl)methanol (1374260-17-9)

Conditions	Yield
Stage #1: tris(8-carboxyl-2,2,6,6-tetramethylbenzo[1,2-d;4,5-d']bis[1,3]dithiol-4-yl)methanol With 1,1'-carbonyldiimidazole In tetrahydrofuran at 55℃; for 4h; Inert atmosphere; Stage #2: 2-(morpholin-4-yl)ethanol In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #3: With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 24h; Inert atmosphere;	96%

2-(morpholin-4-yl)ethanol (622-40-2) + 2-chloro-N-(4-(5-(3,4-dichlorophenyl)-3-hydroxy-1H-1,2,4-triazol-1-yl)phenyl)acetamide → 2-chloro-N-(4-(5-(3,4-dichlorophenyl)-3-(2-morpholinoethoxy)-1H-1,2,4-triazol-1-yl)phenyl)acetamide

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 3h;	96%

2-(morpholin-4-yl)ethanol (622-40-2) + (3'aRS,6'aSR)-1-(cis-4-isopropylcyclohexyl)-2'-phenylhexahydrospiro[piperidine-4,1'-pyrrolo[3,4-c]pyrrole]-4',6'-dione → (3'aRS,6'aSR)-1-(cis-4-isopropylcyclohexyl)-5'-(2-morpholin-4-yl-ethyl)-2'-phenylhexahydrospiro[piperidine-4,1'-pyrrolo[3,4-c]pyrrole]-4',6'-dione

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 24h; Mitsunobu reaction;	95%

2-(morpholin-4-yl)ethanol (622-40-2) + 3-hydroxy-4-methoxybenzoate (6702-50-7) → 4-Methoxy-3-(2-morpholin-4-yl-ethoxy)benzoic acid methyl ester (250726-35-3) + diethyl hydrazodicarboxylate (4114-28-7)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In ethyl acetate	A 95% B n/a

2-(morpholin-4-yl)ethanol (622-40-2) + benzyl (2S,4aS,6aS,6bR,8aS,10S,12aS,12bR,14bR)-10-(chlorocarbonyl)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate → 2-benzyl 10-(2-morpholinoethyl)(2S,4aS,6aS,6bR,8aS,10S,12aS,12bR,14bR)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2,10-dicarboxylate

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃;	95%

2-(morpholin-4-yl)ethanol (622-40-2) + methyl p-toluene sulfonate (80-48-8) → S4-(2-hydroxyethyl)-4-methylmorpholin-4-ium 4-methylbenzenesulfonate (1206209-06-4)

Conditions	Yield
In acetonitrile for 4h; Reflux;	94.4%
In acetonitrile for 4h; Reflux;	87%
In acetonitrile for 4h; Reflux;	84%

2-(morpholin-4-yl)ethanol (622-40-2) + 3-chloro-isonicotinonitrile (68325-15-5) → 3-[2-(morpholin-4-yl)ethoxy]pyridine-4-carbonitrile

Conditions	Yield
Stage #1: 2-(morpholin-4-yl)ethanol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Stage #2: 3-chloro-isonicotinonitrile In tetrahydrofuran; mineral oil at 20℃; for 18h;	94%
Stage #1: 2-(morpholin-4-yl)ethanol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Stage #2: 3-chloro-isonicotinonitrile In tetrahydrofuran; mineral oil at 20℃; for 18h;	94%

2-(morpholin-4-yl)ethanol (622-40-2) + 1-oxo-6-hydroxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (867187-58-4) → 6-(2-morpholine-4-ylethoxy)-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (867187-62-0)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; benzene at 0 - 20℃; for 2h;	93%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; benzene at 0 - 20℃; for 2h;	93%

2-(morpholin-4-yl)ethanol (622-40-2) + 4-fluoro-1-nitro-2-(prop-2-yn-1-yloxy)benzene → 4-(4-nitro-3-(prop-2-ynyloxy)phenoxyethyl)morpholine (1202634-09-0)

Conditions	Yield
Stage #1: 2-(morpholin-4-yl)ethanol With sodium hydride In N,N-dimethyl-formamide at 20℃; Stage #2: 4-fluoro-1-nitro-2-(prop-2-yn-1-yloxy)benzene In N,N-dimethyl-formamide at -35℃; for 6h; Inert atmosphere;	93%

2-(morpholin-4-yl)ethanol (622-40-2) + 4-Iodophenol (540-38-5) → 4-<2-(p-iodophenoxy)ethyl>morpholine (103808-71-5)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; for 17h; Cooling with ice;	93%

2-(morpholin-4-yl)ethanol (622-40-2) + 4-hydroxy-2-nitroaniline (610-81-1) → 4-(2-morpholin-4-yl-ethoxy)-2-nitro-phenylamine

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In ethyl acetate	92%
With diisopropyl (E)-azodicarboxylate; triphenylphosphine In tetrahydrofuran
With diisopropyl (E)-azodicarboxylate; triphenylphosphine In tetrahydrofuran

Upstream product

• 110-91-8 morpholine 
• 107-07-3 2-chloro-ethanol 
• 540-51-2 2-bromoethanol 
• 637-39-8 triethanolamine hydrochloride 
• 141-43-5 ethanolamine 
• 111-44-4 3-oxa-1,5-dichloropentane 
• 624-76-0 Iodoethanol 
• 102-71-6 triethanolamine 
• 3235-82-3 N-morpholylacetic acid ethyl ester 
• 6342-79-6 1,2-dimorpholinoethane-1,2-dione 
• 555-77-1 tris-(2-chloro-ethyl)-amine 
• 34270-90-1 2,2'-diiodoethyl ether 
• 7664-41-7 ammonia 
• 50594-07-5 phenyl-carbamic acid-(2-morpholino-ethyl ester); hydrochloride 

Downstream Products

• 21820-56-4 4-(pyrrolidine-1-sulfonyl)-benzoic acid 2-morpholin-4-yl-ethyl ester 
• 23958-63-6 4-(piperidine-1-sulfonyl)-benzoic acid 2-morpholin-4-yl-ethyl ester 
• 112922-86-8 (2-Ethoxy-phenyl)-carbamic acid 2-morpholin-4-yl-ethyl ester; hydrochloride 
• 85002-98-8 2-(2-morpholinoethoxy)-5-nitropyridine 
• 85003-02-7 2-(2-Cyclohexyl-ethoxy)-5-nitro-pyridine 
• 75926-57-7 5-Nitro-2-phenethyloxy-pyridine 
• 112922-90-4 (3-Propoxy-phenyl)-carbamic acid 2-morpholin-4-yl-ethyl ester; hydrochloride 
• 112922-89-1 (2-Propoxy-phenyl)-carbamic acid 2-morpholin-4-yl-ethyl ester; hydrochloride 
• 112922-92-6 (2-Butoxy-phenyl)-carbamic acid 2-morpholin-4-yl-ethyl ester; hydrochloride 
• 112922-91-5 (4-Propoxy-phenyl)-carbamic acid 2-morpholin-4-yl-ethyl ester; hydrochloride 
• 112922-93-7 (3-Butoxy-phenyl)-carbamic acid 2-morpholin-4-yl-ethyl ester; hydrochloride 
• 112922-94-8 (4-Butoxy-phenyl)-carbamic acid 2-morpholin-4-yl-ethyl ester; hydrochloride 
• 112922-95-9 (2-Pentyloxy-phenyl)-carbamic acid 2-morpholin-4-yl-ethyl ester; hydrochloride 
• 112922-96-0 (3-Pentyloxy-phenyl)-carbamic acid 2-morpholin-4-yl-ethyl ester; hydrochloride 

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By using cheap and innocuous reagents, such as NaClO2, NaOCl, and catalytic amounts of TEMPO, a new environmentally friendly protocol for the selective and catalytic TEMPO C(sp3)-H oxidation of piperazines and morpholines to 2,3-diketopiperazines (2,3-DKP) and 3-morpholinones (3-MPs), respectively, has been developed. This novel direct access to 2,3-DKP from piperazines provides significant advantages over the traditional N-monoacylation/intramolecular C-N cyclization procedure. Additionally, by modulating the amounts of TEMPO, 2-alkoxyamino-3-morpholinone can be prepared from morpholine derivatives, which would enable further functionalization at the C2 position of the morpholine skeleton.

METHOD FOR PRODUCING CIS- AND TRANS-ENRICHED MDACH

A process for preparing trans-enriched MDACH, including: distilling an MDACH starting mixture in the presence of an auxiliary, which is an organic compound having a molar mass of 62 to 500 g/mol, a boiling point at least 5° C. above the boiling point of cis,cis-2,6-diamino-1-methylcyclohexane, and 2 to 4 functional groups, each of which is independently an alcohol group or a primary, secondary or tertiary amino group. The MDACH starting mixture includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, based on the total amount of MDACH present in the MDACH starting mixture. The MDACH starting mixture includes both trans and cis isomers. Trans-enriched MDACH includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, where the proportion of trans isomers in the mixture is higher than the proportion of trans isomers in the MDACH starting mixture.