27514-08-5

Basic information

• Product Name: N-(4-Oxocyclohexyl)acetamide
• Synonyms: N-(4-OXOCYCLOHEXYL)ACETAMIDE;4-N-ACETYL-AMINO-CYCLOHEXANONE;4-ACETAMIDOCYCLOHEXANONE;4-ACETAMINO CYCLOHEXANONE;N-4-acetylaminocyclohexanone;(2-hydroxyphenyl)-(4-methylphenyl)methanone;4-N-Acetyl-aMinocyclohexanoe;AcetaMide,N-(4-oxocyclohexyl)-
• CAS NO: 27514-08-5
• Molecular Formula: C₈H₁₃NO₂
• Molecular Weight: 155.19
• EINECS: 1806241-263-5
• Product Categories: (intermediate of pramipexole);organic intermediates
• Mol File: 27514-08-5.mol
• Article Data: 16

Chemical Properties

• Melting Point: 137 °C
• Boiling Point: 359.086 °C at 760 mmHg
• Flash Point: 168.906 °C
• Appearance: Off-white/Solid
• Density: 1.071 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.476
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 15.76±0.20(Predicted)
• CAS DataBase Reference: N-(4-Oxocyclohexyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-Oxocyclohexyl)acetamide(27514-08-5)
• EPA Substance Registry System: N-(4-Oxocyclohexyl)acetamide(27514-08-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39
• WGK Germany: 3
• Hazardous Substances Data: 27514-08-5(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

N-(4-Oxocyclohexyl)acetamide is a metabolite of (trans-N-(4-nitroxycyclohexyl)acetamide (CAS 137213-91-3). N-(4-Oxocyclohexyl)acetamide has been used as a reactant in the preparation of 2-Pyrimidinecarbonitrile derivatives as falcipain inhibitors and antiparasitic agents.

InChI:InChI=1/C8H13NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h7H,2-5H2,1H3,(H,9,10)

Synthetic route

trans-N-acetyl-4-hydroxycyclohexylamine (23363-88-4) → N-(4-oxocyclohexyl)acetamide (27514-08-5)

Conditions	Yield
With Jones reagent In acetone at 0 - 30℃;	85%
With Jones Reagens In water at 20℃;	78%
With sodium dichromate; sulfuric acid In water for 0.333333h;	72%

N-((trans)-4-hydroxycyclohexyl)acetamide (27489-60-7) → N-(4-oxocyclohexyl)acetamide (27514-08-5)

Conditions	Yield
With chromium(VI) oxide; sulfuric acid at 20℃; for 22h; Oxidation;	74%

2-(4-Acetylamino-cyclohexylideneamino)-propionamide (142080-48-6) → N-(4-oxocyclohexyl)acetamide (27514-08-5) + alanine amide (4726-84-5)

Conditions	Yield
With sodium hydroxide In acetonitrile at 20℃; Rate constant; Kinetics; var. temp.;

4-acetaminophenol (103-90-2) → N-cyclohexylacetamide (1124-53-4) + N-((trans)-4-hydroxycyclohexyl)acetamide (27489-60-7) + cis-(N-4-hydroxycyclohexyl)acetamide (27489-61-8) + N-(4-oxocyclohexyl)acetamide (27514-08-5)

Conditions	Yield
With hydrogen; RuC In ethanol at 119.85℃; under 37503 Torr; Product distribution; Further Variations:; Catalysts; Solvents;

trans-4-hydroxycyclohexylamine (27489-62-9) → N-(4-oxocyclohexyl)acetamide (27514-08-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / 1 h / Heating 2: 97 percent / 1M aq. NaOH / 0.5 h / 20 °C 3: 74 percent / CrO3; aq. H2SO4 / 22 h / 20 °C View Scheme

trans-4-(acetylamino)cyclohexyl acetate (90978-87-3) → N-(4-oxocyclohexyl)acetamide (27514-08-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / 1M aq. NaOH / 0.5 h / 20 °C 2: 74 percent / CrO3; aq. H2SO4 / 22 h / 20 °C View Scheme

4-acetaminophenol (103-90-2) → N-(4-oxocyclohexyl)acetamide (27514-08-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Raney nickel / ethanol / 3 h / 180 °C / 90500.9 Torr 2: 72 percent / sodium dichromate dihydrate, conc. H2SO4 / H2O / 0.33 h View Scheme
With borax; hydrogen In diethylene glycol dimethyl ether
With palladium on activated charcoal; hydrogen In aq. acetate buffer at 105℃; under 4500.45 Torr; pH=10;

acetyl chloride (75-36-5) + 4‐aminocyclohexanone → N-(4-oxocyclohexyl)acetamide (27514-08-5)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 18h;

4-acetaminophenol (103-90-2) → trans-N-acetyl-4-hydroxycyclohexylamine (23363-88-4) + N-(4-oxocyclohexyl)acetamide (27514-08-5)

Conditions	Yield
With hydrogen In ethanol at 170℃; under 37503.8 Torr; for 0.333333h; Autoclave;
With hydrogen In ethanol at 170℃; under 37503.8 Torr; for 0.333333h; Autoclave;

N-(4-oxocyclohexyl)acetamide (27514-08-5) → 4-aminocyclohexan-1-one hydrochloride

Conditions	Yield
With hydrogenchloride for 6h; Heating;	100%

N-(4-oxocyclohexyl)acetamide (27514-08-5) → 2-bromo-4-acetamidocyclohexanone (687639-03-8)

Conditions	Yield
With bromine In chloroform at 22℃; for 0.333333h;	100%
With bromine; acetic acid at 60℃; for 1h;
With bromine In water at 45℃;

N-(4-oxocyclohexyl)acetamide (27514-08-5) + malononitrile (109-77-3) → N-(4-(dicyanomethylene)cyclohexyl)acetamide

Conditions	Yield
With ammonium acetate; acetic acid In benzene at 130℃; Knoevenagel Condensation; Dean-Stark;	97%

N-(4-oxocyclohexyl)acetamide (27514-08-5) + 3-amino-N,N'-dihydroxyfurazan-4-carboximidamide → N-(3-(3-aminofurazan-4-yl)-4-hydroxy-1-oxo-2,4-diazaspiro[4,5]decane-2-en-8-yl)acetamide

Conditions	Yield
In methanol at 20 - 25℃; for 3h;	94%
In methanol at 20℃; for 1h;	91%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + N-(4-oxocyclohexyl)acetamide (27514-08-5) → ethyl 2-(trans/cis)-(4-acetamidocyclohexyl)acetate

Conditions	Yield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With potassium tert-butylate In tetrahydrofuran at 0 - 5℃; for 1h; Wittig-Horner Reaction; Stage #2: N-(4-oxocyclohexyl)acetamide In tetrahydrofuran at 0 - 20℃; for 2h; Stage #3: With palladium 10% on activated carbon; hydrogen at 20℃; under 760.051 Torr; for 24h;	92.6%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With potassium tert-butylate In tetrahydrofuran at 0 - 5℃; for 1h; Wittig-Horner Reaction; Stage #2: N-(4-oxocyclohexyl)acetamide In tetrahydrofuran at 0 - 20℃; for 2h; Wittig-Horner Reaction; Stage #3: With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; ethyl acetate at 20℃; under 760.051 Torr; for 24h;	90%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester; N-(4-oxocyclohexyl)acetamide With potassium tert-butylate In tetrahydrofuran at 0 - 5℃; Stage #2: With 5%-palladium/activated carbon; hydrogen In ethyl acetate at 20℃;

benzophenone (119-61-9) + N-(4-oxocyclohexyl)acetamide (27514-08-5) → N-(4-benzhydrylidenecyclohexyl)acetamide + N-(4'-acetylamino-bicyclohexyliden-4-yl)-acetamide + 1,1,2,2-tetraphenylethylene (632-51-9)

Conditions	Yield
With pyridine; titanium tetrachloride; zinc In tetrahydrofuran Cross McMurry reaction; Heating;	A 90.5% B 2% C 4%

quinolin-5-yl-hydrazine (15793-79-0) + N-(4-oxocyclohexyl)acetamide (27514-08-5) → N-[4-(Quinolin-5-yl-hydrazono)-cyclohexyl]-acetamide (102745-87-9)

Conditions	Yield
In ethanol for 0.333333h; Heating;	89%

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + N-(4-oxocyclohexyl)acetamide (27514-08-5) → methyl N-(4-acetamidophenyl)-L-phenylalaninate

Conditions	Yield
With styrene In 1,4-dioxane; water at 140℃; under 3750.38 Torr; for 5h; Catalytic behavior; Flow reactor; enantioselective reaction;	88%

4-ethylpiperazine (5308-25-8) + N-(4-oxocyclohexyl)acetamide (27514-08-5) → N-(4-(4-ethylpiperazin-1-yl)cyclohexyl)acetamide (1214265-83-4)

Conditions	Yield
Stage #1: 4-ethylpiperazine; N-(4-oxocyclohexyl)acetamide With methanesulfonic acid In toluene for 5h; Reflux; Stage #2: With sodium tetrahydroborate; ethanol In toluene at 15 - 20℃; Inert atmosphere;	87%

N-(4-oxocyclohexyl)acetamide (27514-08-5) → N-(4-(hydroxyimino)cyclohexyl)acetamide

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In ethanol; water at 100℃;	87%

pyrrolidine (123-75-1) + N-(4-oxocyclohexyl)acetamide (27514-08-5) → N-(4-Pyrrolidinocyclohex-3-enyl)acetamid (102745-76-6)

Conditions	Yield
In toluene for 3h; Heating;	85%
In benzene for 4.5h; Heating;
In toluene for 18h; Molecular sieve; Reflux;

benzyl 2,2-dihydroxy-3-oxobutanoate + N-(4-oxocyclohexyl)acetamide (27514-08-5) → benzyl 2-(5-acetamido-2-oxocyclohexyl)-2-hydroxy-3-oxobutanoate

Conditions	Yield
With L-proline In dichloromethane at 20℃; for 32h;	85%

N-(4-oxocyclohexyl)acetamide (27514-08-5) + ethylene glycol (107-21-1) → N-(1,4-Dioxaspiro<4.5>dec-8-yl)acetamid (127686-18-4)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 4h; Heating;	80%

N-(4-oxocyclohexyl)acetamide (27514-08-5) → N-acetyl-p-phenylenediamine (122-80-5)

Conditions	Yield
With ethene; 5%-palladium/activated carbon; ammonium acetate; potassium carbonate In acetonitrile at 90℃; under 760.051 Torr; for 15h; Reagent/catalyst; Schlenk technique;	80%
With styrene; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 130℃; for 20h; Sealed tube; Inert atmosphere;	65%

N-(4-oxocyclohexyl)acetamide (27514-08-5) + orthoformic acid triethyl ester (122-51-0) → 4-acetamido-1-ethoxycyclohexene (73625-13-5)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 25℃; for 16h;	78%

2',4'-dihydroxy-4-acetophenone (89-84-9) + N-(4-oxocyclohexyl)acetamide (27514-08-5) → C16H19NO4

Conditions	Yield
With pyrrolidine In acetonitrile at 50℃; for 12h;	77.1%

N-(4-oxocyclohexyl)acetamide (27514-08-5) + toluene-4-sulfonamide (70-55-3) → N-(4-(4-methylphenylsulfonamido)phenyl)acetamide (27022-64-6)

Conditions	Yield
With 1,10-Phenanthroline; palladium(II) trifluoroacetate; oxygen In toluene at 140℃; for 40h;	76%

N-(4-oxocyclohexyl)acetamide (27514-08-5) + 2-amino-phenol (95-55-6) → N-((5aS*,11aS*,15S*)-6,12-dihydro-5a,11a-butanobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazin-15-yl)acetamide

Conditions	Yield
With sulfur; acetic acid; dimethyl sulfoxide at 80℃; for 16h; Inert atmosphere; stereoselective reaction;	76%

1-(1-methylethyl)piperazine (4318-42-7) + N-(4-oxocyclohexyl)acetamide (27514-08-5) → N-(4-(4-i-propylpiperazin-1-yl)cyclohexyl)acetamide (1214265-87-8)

Conditions	Yield
Stage #1: 1-(1-methylethyl)piperazine; N-(4-oxocyclohexyl)acetamide With methanesulfonic acid In toluene for 5h; Reflux; Stage #2: With sodium tetrahydroborate; ethanol In toluene at 15 - 20℃; Inert atmosphere;	75.6%

N-(4-oxocyclohexyl)acetamide (27514-08-5) + thiourea (17356-08-0) → 2-amino-6-acetylamino-4,5,6,7-tetrahydrobenzothiazole

Conditions	Yield
With bromine In acetic acid at 20 - 30℃; for 5h; Reflux;	75%

1-n-propylpiperazine (21867-64-1) + N-(4-oxocyclohexyl)acetamide (27514-08-5) → N-(4-(4-propylpiperazin-1-yl)cyclohexyl)acetamide (1214265-85-6)

Conditions	Yield
Stage #1: 1-n-propylpiperazine; N-(4-oxocyclohexyl)acetamide With methanesulfonic acid In toluene for 5h; Reflux; Stage #2: With sodium tetrahydroborate; ethanol In toluene at 15 - 20℃; Inert atmosphere;	73%

N-(4-oxocyclohexyl)acetamide (27514-08-5) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → N-<3-<(dimethylamino)methylene>-4-oxocyclohexyl>acetamide

Conditions	Yield
With triethylamine In benzene Condensation; Heating;	72%
With triethylamine In benzene for 5.25h; Heating;	57%

N-(4-oxocyclohexyl)acetamide (27514-08-5) + nitrobenzene (98-95-3) → 4-Acetamido-N-phenylaniline (38674-90-7)

Conditions	Yield
With palladium diacetate; XPhos In 1-methyl-pyrrolidin-2-one at 150℃; for 24h; Inert atmosphere; Sealed vessel;	72%

1-methyl-piperazine (109-01-3) + N-(4-oxocyclohexyl)acetamide (27514-08-5) → N-(4-(4-methylpiperazin-1-yl)cyclohexyl)acetamide (1214265-81-2)

Conditions	Yield
Stage #1: 1-methyl-piperazine; N-(4-oxocyclohexyl)acetamide With methanesulfonic acid In toluene for 5h; Reflux; Stage #2: With sodium tetrahydroborate; ethanol In toluene at 15 - 20℃; Inert atmosphere;	71%

N-(4-oxocyclohexyl)acetamide (27514-08-5) + 4R-4-hydroxyproline (51-35-4) → N-(cis-9-oxo-5,6,7,8,8a,9-hexahydro-4aH-pyrrolo[1,2-a]indol-7-yl)acetamide

Conditions	Yield
With propionic acid In toluene at 140℃; for 12h; Inert atmosphere; Schlenk technique; stereoselective reaction;	70%

N-(4-oxocyclohexyl)acetamide (27514-08-5) + 1,2-diamino-benzene (95-54-5) → N-(quinoxalino[2,3-a]phenazin-6-yl)acetamide

Conditions	Yield
With sulfur; dimethyl sulfoxide; trifluoroacetic acid at 100℃; for 16h; Inert atmosphere;	70%

N-(4-oxocyclohexyl)acetamide (27514-08-5) + aniline (62-53-3) → 4-Acetamido-N-phenylaniline (38674-90-7)

Conditions	Yield
With 1,10-Phenanthroline; oxygen; palladium diacetate In toluene at 135℃; for 37h; Sealed tube;	65%

N-(4-oxocyclohexyl)acetamide (27514-08-5) + N-Cyanoguanidine (127099-85-8, 780722-26-1) → (+/-)-N-(2,4-diamino-5,6,7,8-tetrahydro-6-quinazolinyl)acetamide

Conditions	Yield
at 180℃; for 1.5h; Condensation;	63%

Upstream product

• 103-90-2 4-acetaminophenol 
• 75-36-5 acetyl chloride 
• 87976-86-1 4‐aminocyclohexanone 
• 90978-87-3 trans-4-(acetylamino)cyclohexyl acetate 
• 27489-62-9 trans-4-hydroxycyclohexylamine 
• 27489-60-7 N-((trans)-4-hydroxycyclohexyl)acetamide 
• 142080-48-6 2-(4-Acetylamino-cyclohexylideneamino)-propionamide 
• 23363-88-4 trans-N-acetyl-4-hydroxycyclohexylamine 

Downstream Products

• 142080-48-6 2-(4-Acetylamino-cyclohexylideneamino)-propionamide 
• 687639-03-8 2-bromo-4-acetamidocyclohexanone 
• 372982-92-8 tert-butyl 2-[[(1R)-2-((2S)-{[(2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-yl)amino]carbonyl}pyrrolidinyl)-1-(cyclohexylmethyl)-2-oxoethyl](tert-butyoxycarbonyl)amino]acetate 
• 372982-56-4 tert-butyl (1R)-2-((2S)-2-{[(2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-yl)amino]carbonyl}pyrrolidinyl)-1-(3,4-dichlorobenzyl)-2-oxoethylcarbamate 
• 372982-57-5 {(R)-1-[(S)-2-(2-Amino-4,5,6,7-tetrahydro-benzothiazol-6-ylcarbamoyl)-pyrrolidine-1-carbonyl]-2,2-diphenyl-ethyl}-carbamic acid tert-butyl ester 
• 106006-80-8 N-(2-amino-4,5,6,7-tetrahydrobenzo[1,2-d]thiazol-6-yl)acetamide 
• 675112-40-0 4-aminocyclohexan-1-one hydrochloride 
• 73625-13-5 4-acetamido-1-ethoxycyclohexene 
• 102745-87-9 N-[4-(Quinolin-5-yl-hydrazono)-cyclohexyl]-acetamide 
• 102745-76-6 N-(4-Pyrrolidinocyclohex-3-enyl)acetamid 

Relevant articles and documents

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Selective hydrogenation of paracetamol to acetamidocyclohexanone with silylated SiO2 supported Pd-based catalysts

A series of catalysts comprising well-distributed Pd nanoparticles incorporated on silylated SiO2 were fabricated by the wet impregnation method and investigated in the selective hydrogenation of paracetamol to 4-acetamidocyclohexanone. The catalysts calcined at different temperatures were characterized by TG, FT-IR, N2 physisorption, TPR and XPS. The results showed that organic modification led to a catalyst surface composed of stable Si-(CH3)3 species even after calcination at 300 °C. Also, changes occurred in the size and electronic properties of the Pd particles through the different amounts of grafted groups on the SiO2 support. The mode of adsorption of the paracetamol molecule was influenced by the quite bulky organic groups on the support, resulting in a significant improvement in selectivity towards 4-acetamidocyclohexanone and preventing full hydrogenation to some extent. The best result was obtained on the silylated Pd catalyst calcined at 500 °C, with 64.9% selectivity to keto at the paracetamol conversion of 60.5%, while the non-silylated SiO2 supported Pd catalyst gave 4-acetamidocyclohexanone selectivity of 29.1% at 53.8% conversion.

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