3612-18-8

Basic information

• Product Name: 1-Ethyl-4-piperidone
• Synonyms: 4-Piperidinone,1-ethyl-;1-ETHYL-4-PIPERIDONE;Ethyl 1-piperidone;1-Ethylpiperidin-4-one 98%;1-ETHYL-4-PIPERIDONE 98%;1-Ethyl-4-piperidone,98%;1-Ethyl-4-oxopiperidine;N-ETHYL-4-PIPERIDONE
• CAS NO: 3612-18-8
• Molecular Formula: C₇H₁₃NO
• Molecular Weight: 127.18
• EINECS: 222-781-9
• Product Categories: Amines;blocks;Piperidine;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Piperidones;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 3612-18-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 30-32C
• Boiling Point: 46-48 °C1 mm Hg(lit.)
• Flash Point: 156 °F
• Appearance: clear yellow to brown viscous liquid
• Density: 0.944 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.219mmHg at 25°C
• Refractive Index: n20/D 1.464(lit.)
• Storage Temp.: 2-8°C
• PKA: 8.10±0.20(Predicted)
• Water Solubility: Miscible in water.
• BRN: 107533
• CAS DataBase Reference: 1-Ethyl-4-piperidone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Ethyl-4-piperidone(3612-18-8)
• EPA Substance Registry System: 1-Ethyl-4-piperidone(3612-18-8)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 45-36/37/39-26-36
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 3612-18-8(Hazardous Substances Data)

Usage

Uses

1-Ethyl-4-piperidone has been used in the preparation of 3,5-bisarylmethylene-1-ethyl-4-piperidones.

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 1239, 1946 DOI: 10.1021/ja01211a028

InChI:InChI=1/C7H13NO/c1-2-8-5-3-7(9)4-6-8/h2-6H2,1H3/p+1

Synthetic route

ethyl 1-ethyl-4-oxopiperidine-3-carboxylate (99329-51-8) → N-ethyl-4-piperidone (3612-18-8)

Conditions	Yield
With hydrogenchloride Heating;	93%

ethyl bromide (74-96-4) + 4-piperidone hydrochloride (41979-39-9) → N-ethyl-4-piperidone (3612-18-8)

Conditions	Yield
With potassium carbonate In acetonitrile for 21h;	62%
With sodium carbonate In water; acetonitrile at 85℃;

8-Ethyl-1,4-dioxa-8-aza-spiro[4.5]decane → N-ethyl-4-piperidone (3612-18-8)

Conditions	Yield
With hydrogenchloride In acetone for 12h; Heating;

ethyl 3-[N-ethyl-N-(2-ethoxycarbonylethyl)amino]propionate (3619-64-5) → N-ethyl-4-piperidone (3612-18-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / NaH / toluene; ethanol / Heating 2: 93 percent / conc. aq. HCl / Heating View Scheme

4,4-ethylenedioxy-piperidine (177-11-7) → N-ethyl-4-piperidone (3612-18-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / CHCl3 / 18 h / Heating 2: LiAlH4 / diethyl ether / 18 h / 0 °C 3: 5percent HCl / acetone / 12 h / Heating View Scheme

1-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)ethanone (176910-35-3) → N-ethyl-4-piperidone (3612-18-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether / 18 h / 0 °C 2: 5percent HCl / acetone / 12 h / Heating View Scheme

piperidin-4-one (41661-47-6) + ethyl bromide (74-96-4) → N-ethyl-4-piperidone (3612-18-8)

Conditions	Yield
With hydrogenchloride; potassium carbonate In ethanol Reflux;

piperidin-4-one (41661-47-6) + ethyl halide → N-ethyl-4-piperidone (3612-18-8)

Conditions	Yield
With potassium carbonate In dichloromethane at 0 - 20℃;

4-piperidone hydrochloride (41979-39-9) + ethyl iodide (75-03-6) → N-ethyl-4-piperidone (3612-18-8)

Conditions	Yield
With potassium carbonate In ethanol for 2h; Reflux;

N-ethyl-4-piperidone (3612-18-8) + potassium cyanide + ammonium carbonate (506-87-6) → 8-ethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione

Conditions	Yield
In methanol; water at 90℃; for 0.166667h; Bucherer-Bergs Reaction; Sealed tube; Microwave irradiation;	99.8%

N-ethyl-4-piperidone (3612-18-8) + methyl iodide (74-88-4) → 1-methyl-1-ethyl-4-oxopiperidinium iodide (77542-18-8)

Conditions	Yield
In acetone at 20℃; for 18h;	95%
In acetone at 20 - 25℃; for 23h;	95%
In acetone at 0 - 20℃; for 6h;	95%

N-ethyl-4-piperidone (3612-18-8) + 4-fluorobenzaldehyde (459-57-4) → 3E,5E-3,5-bis[(4-fluorophenyl)methylidene]-1-ethyl-4-piperidone

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 0.5h;	95%
In ethanol	57.7%
With potassium hydroxide In methanol at 25℃;

N-ethyl-4-piperidone (3612-18-8) + 4-methyl-benzaldehyde (104-87-0) → 1-ethyl-3,5-bis(4-methylbenzylidene)piperid in-4-one (330657-31-3)

Conditions	Yield
With potassium hydroxide In ethanol; water at 20℃; for 0.5h;	95%

N-ethyl-4-piperidone (3612-18-8) + bis(trimethylsilyl)phosphonite (30148-50-6) → trimethylsilyl 1-ethyl-4-(trimethylsiloxy)piperidin-4-ylphosphinate

Conditions	Yield
In dichloromethane at 0 - 5℃; Inert atmosphere;	93%

N-ethyl-4-piperidone (3612-18-8) + 2,4-dichlorobenzaldeyhde (874-42-0) → 3E,5E-3,5-bis[(2,4-dichlorophenyl)methylidene]-1-ethyl-4-piperidone (1434133-38-6)

Conditions	Yield
With sodium hydroxide In ethanol; water at 5 - 8℃; Aldol Condensation;	92.21%
With potassium hydroxide In methanol at 25℃; for 3h;	88%

N-ethyl-4-piperidone (3612-18-8) + 4-chlorobenzaldehyde (104-88-1) → 3,5-Bis-[1-(4-chloro-phenyl)-meth-(E)-ylidene]-1-ethyl-piperidin-4-one

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 0.5h;	92%
With sodium hydroxide In ethanol; water at 20℃;

N-ethyl-4-piperidone (3612-18-8) + o-hydroxyacetophenone (118-93-4) → 1'-ethylspiro[chromene-2,4'-piperidin]-4(3H)-one (1630952-43-0)

Conditions	Yield
With pyrrolidine In ethanol for 24h; Inert atmosphere; Reflux;	92%

N-ethyl-4-piperidone (3612-18-8) + anthranilic acid (118-92-3) → 10-chloro-2-ethyl-1,2,3,4-tetrahydro-benzo[b][1,6]naphthyridine

Conditions	Yield
With phosphorus (III) oxychloride at 60℃; for 5h;	91%

N-ethyl-4-piperidone (3612-18-8) + anthranilic acid (118-92-3) → 10-chloro-2-ethyl-1,2,3,4-tetrahydro-benzo[b][1,6]naphthyridine + 2-aminobenzoyl chloride (21563-73-5)

Conditions	Yield
With trichlorophosphate at 60℃; for 5h;	A 91% B n/a
With phosphorus (III) oxychloride for 2h; Heating;

N-ethyl-4-piperidone (3612-18-8) + 4-bromo-benzaldehyde (1122-91-4) → 3,5-Bis-[1-(4-bromo-phenyl)-meth-(E)-ylidene]-1-ethyl-piperidin-4-one

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 0.5h;	90%
With sodium hydroxide In ethanol; water at 20℃;

2-bromothiophene (1003-09-4) + N-ethyl-4-piperidone (3612-18-8) → 1-ethyl-1,2,3,6-tetrahydro-4-(thiophen-2-yl)pyridine (1046478-49-2)

Conditions	Yield
Stage #1: N-ethyl-4-piperidone With tris-(dibenzylideneacetone)dipalladium(0); toluene-4-sulfonic acid hydrazide; lithium tert-butoxide; XPhos In 1,4-dioxane for 0.0166667h; Inert atmosphere; Stage #2: 2-bromothiophene In 1,4-dioxane at 110℃; for 5h; Inert atmosphere;	90%

N-ethyl-4-piperidone (3612-18-8) + Cyanothioacetamide (7357-70-2) + malononitrile (109-77-3) → 10-amino-7,11-dicyano-3-ethyl-9-aza-3-azoniaspiro[5.5]undeca-7,10-diene-8-thiolate (311333-66-1)

Conditions	Yield
In ethanol at 20℃; for 2h;	90%

p-diethylamino-cinnamaldehyde (22411-59-2) + N-ethyl-4-piperidone (3612-18-8) → (3E,5E)-3,5-bis{(2E)-3-[4-(diethylamino)phenyl]prop-2-en-1-ylidene}-1-ethylpiperidin-4-one (1427057-62-2)

Conditions	Yield
With boron trifluoride diethyl etherate In acetonitrile Aldol Condensation;	90%

N-ethyl-4-piperidone (3612-18-8) + piperidine-4-sulfonic acid amide monohydrochloride → 1'-ethyl-[1,4'-bipiperidine]-4-sulfonamide

Conditions	Yield
With sodium tris(acetoxy)borohydride; triethylamine In acetonitrile for 20h;	90%

N-ethyl-4-piperidone (3612-18-8) + 2-Trifluoromethylbenzaldehyde (447-61-0) → N-ethyl-3,5-bis-(2-(trifluoromethyl)benzylidene)piperidin-4-one

Conditions	Yield
With sodium hydroxide In ethanol at 8℃; for 12h;	89.5%

thiophene-2-carbaldehyde (98-03-3) + N-ethyl-4-piperidone (3612-18-8) → 1-ethyl-3,5-bis(thien-2-yl-methyl-ene)-piperidin-4-one (728901-55-1)

Conditions	Yield
With sodium hydroxide In ethanol at 20℃; for 0.5h;	89%

N-ethyl-4-piperidone (3612-18-8) + cyanoselenoacetamide (96517-60-1) → 10-amino-7,11-dicyano-3-ethyl-9-aza-3-azoniaspiro[5,5]undeca-7,10-diene-8-selenolate (1447544-61-7)

Conditions	Yield
In ethanol at 20℃; for 24h; Inert atmosphere;	89%

N-ethyl-4-piperidone (3612-18-8) + ethyl 2-cyanoacetate (105-56-6) → C13H16N4O2

Conditions	Yield
With ammonium hydroxide; ammonium acetate In methanol at 0 - 10℃; for 10h; Large scale;	89%

N-ethyl-4-piperidone (3612-18-8) + 3-acetyl-1-phenyl-2-pentene-1,4-dione (89201-18-3) → 6-acetyl-1'-ethyl-5-methyl-3a-phenyl-3a,6a-dihydrospiro[furo[2,3-d][1,3]dioxole-2,4'-piperidine]

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at -40℃; for 3h; Solvent; Temperature; Inert atmosphere;	88%

N-ethyl-4-piperidone (3612-18-8) + benzaldehyde (100-52-7) → (3E,5E)-3,5-dibenzylidene-1-ethylpiperidin-4-one

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 0.5h;	87%

N-ethyl-4-piperidone (3612-18-8) + 2,5-dimethoxybenzaldehyde (93-02-7) → (3E,5E)-3,5-bis(2,5-dimethoxybenzylidene)-1-ethylpiperidin-4-one

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 0.5h;	87%
With sodium hydroxide In ethanol; water at 5 - 8℃; Aldol Condensation;	69.01%

N-ethyl-4-piperidone (3612-18-8) + 4,6-dimethylthieno[2,3-b]pyridine-3(2H)-one (55023-32-0) + malononitrile (109-77-3) → C19H22N4OS

Conditions	Yield
With triethylamine In ethanol at 40 - 60℃;	86%

N-ethyl-4-piperidone (3612-18-8) + 5-bromo-1H-indole (10075-50-0) → 5-(1-ethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (1046478-53-8)

Conditions	Yield
Stage #1: N-ethyl-4-piperidone With tris-(dibenzylideneacetone)dipalladium(0); toluene-4-sulfonic acid hydrazide; lithium tert-butoxide; XPhos In 1,4-dioxane for 0.0166667h; Inert atmosphere; Stage #2: 5-bromo-1H-indole In 1,4-dioxane at 110℃; for 5h; Inert atmosphere;	86%

N-ethyl-4-piperidone (3612-18-8) + 3-(4-dimethylamino-phenyl)-propenal (20432-35-3, 6203-18-5) → (3E,5E)-3,5-bis{(2E)-3-[4-(dimethylamino)phenyl]prop-2-en-1-ylidene}-1-ethylpiperidin-4-one (1427057-61-1)

Conditions	Yield
With boron trifluoride diethyl etherate In acetonitrile Aldol Condensation;	86%

N-ethyl-4-piperidone (3612-18-8) + toluene-4-sulfonic acid hydrazide (1576-35-8) → N'-(1-ethylpiperidin-4-ylidene)-4-methylbenzenesulfonohydrazide (574717-86-5)

Conditions	Yield
With pyridinium p-toluenesulfonate In ethanol Reflux;	86%

N-ethyl-4-piperidone (3612-18-8) + 3,4-dimethoxy-benzaldehyde (120-14-9) → (3E,5E)-3,5-bis(3,4-dimethoxybenzylidene)-1-ethylpiperidin-4-one

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 0.5h;	85%
With sodium hydroxide In ethanol; water at 5 - 8℃; Aldol Condensation;	66.32%

N-ethyl-4-piperidone (3612-18-8) + tert‐butyl piperidin‐4‐ylcarbamate (73874-95-0) → tert-butyl 1'-(ethyl)-1,4'-bipiperidin-4-ylcarbamate (1214265-91-4)

Conditions	Yield
Stage #1: N-ethyl-4-piperidone; (piperidin-4-yl)carbamic acid tert-butyl ester With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran Stage #2: With sodium carbonate In water	85%

N-ethyl-4-piperidone (3612-18-8) + 2-methylprop-1-enyl chloride (513-37-1) → 1-ethyl-1-(2-methylallyl)-4-oxopiperidine-1-ium iodide

Conditions	Yield
Stage #1: 2-methylprop-1-enyl chloride With sodium iodide In acetone at 20℃; for 5h; Stage #2: N-ethyl-4-piperidone In acetone at 50℃; for 8h;	85%

Upstream product

• 99329-51-8 ethyl 1-ethyl-4-oxopiperidine-3-carboxylate 
• 41979-39-9 4-piperidone hydrochloride 
• 75-03-6 ethyl iodide 
• 41661-47-6 piperidin-4-one 
• 74-96-4 ethyl bromide 
• 176910-35-3 1-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)ethanone 
• 177-11-7 4,4-ethylenedioxy-piperidine 
• 3619-64-5 ethyl 3-[N-ethyl-N-(2-ethoxycarbonylethyl)amino]propionate 

Downstream Products

• 86219-68-3 1-ethyl-4-phenyl-piperidin-4-ol 
• 2805-51-8 1-ethyl-4-(4-fluoro-benzyl)-piperidin-4-ol 
• 872817-32-8 1-ethyl-4-(4-methoxy-phenyl)-piperidin-4-ol 
• 50534-45-7 4-amino-N-ethylpiperidine 
• 3518-83-0 1-ethylpiperidin-4-ol 
• 179327-28-7 (2-amino-6-ethyl-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-3-yl)-(3,4-dimethoxy-phenyl)-methanone 
• 276863-64-0 1-ethyl-piperidine-4-thiol 
• 7069-88-7 3,5-dibenzylidene-1-ethyl-piperidin-4-one 
• 7058-73-3 1-ethyl-3,5-bis(4-methoxyhenzylidene)piperidin-4-one 
• 7073-14-5 3,5-bis-(4-dimethylamino-benzylidene)-1-ethyl-piperidin-4-one 
• 14749-62-3 propionic acid-(1-ethyl-4-phenyl-[4]piperidyl ester) 
• 710350-60-0 4-amino-4-cyano-1-ethylpiperidine 
• 59119-23-2 4-hydroxy-4-cyano-1-ethyl piperidine 

Relevant articles and documents

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Discovery of tetrahydropyrido[4,3-d]pyrimidine derivatives for the treatment of neuropathic pain

A series of tetrahydropyridopyrimidine derivatives were synthesized and evaluated for neurotoxicity and peripheral analgesic activity followed by assessment of antiallodynic and antihyperalgesic potential in two peripheral neuropathic pain models, the chronic constriction injury (CCI) and partial sciatic nerve ligation (PSNL). Compounds (4b and 4d) exhibiting promising efficacies in four behavioral assays of allodynia and hyperalgesia (spontaneous pain, tactile allodynia, cold allodynia and mechanical hyperalgesia) were quantified for their ED50 values (15.12-65.10 mg/kg). Studies carried out to assess the underlying mechanism revealed that the compounds suppressed the inflammatory component of the neuropathic pain and prevented oxidative and nitrosative stress.

DIHYDROIMIDAZO [ 1, 5-F] PTERIDINES AS POLO-LIKE KINASE INHIBITORS

The present invention provides PLK inhibitors of the formula (I) wherein the variables are as defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds; methods and intermediates useful for making the compounds; and methods of using the compounds.