41979-39-9

Basic information

• Product Name: 4-oxopiperidinium chloride
• Synonyms: 4-oxopiperidinium chloride;4-Piperidone Hcl;PIPERIDIN-4-ONE,HCL;Piperidine-4-one·hydrochloride;4-Piperidinone hydrochloride;Nsc134482;4-Piperidinone,hydrochloride (1:1);4-Oxopiperidinium chloride hydrochloride
• CAS NO: 41979-39-9
• Molecular Formula: C₅H₉NO*ClH
• Molecular Weight: 135.592
• EINECS: 255-602-8
• Mol File: 41979-39-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 145.5-147 °C(Solv: acetonitrile (75-05-8))
• Boiling Point: 175.1 °C at 760 mmHg
• Flash Point: 84.6 °C
• Appearance: /
• Density: 1.001 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-oxopiperidinium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-oxopiperidinium chloride(41979-39-9)
• EPA Substance Registry System: 4-oxopiperidinium chloride(41979-39-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 41979-39-9(Hazardous Substances Data)

Usage

Physical Form

White to yellow solid

synthesis

To a solution of tert-butyl 4-oxopiperidine-1-carboxylate (2300 g, 11.6 mol) in 1,4-dioxane was added a solution of HCl (g)/1,4-dioxane (4 L, 10 mol/L) slowly at 0°C. After the addition, the reaction mixture was stirred for 4 h and TLC (EtOAc/petroleum ether = 1:5) showed the reaction was complete. The solvent was removed in vacuo to afford piperidin-4-one hydrochloride as a brown solid.Fig The synthetic method of 4-oxopiperidinium chloride

Uses

4-oxopiperidinium chloride is a useful research chemical.

InChI:InChI=1/C5H9NO.ClH/c7-5-1-3-6-4-2-5;/h6H,1-4H2;1H

Synthetic route

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → 4-piperidone hydrochloride (41979-39-9)

Conditions	Yield
With hydrogenchloride In methanol at 0 - 20℃;	100%
With hydrogenchloride In 1,4-dioxane at 0 - 20℃; for 2h;	99%
With hydrogenchloride In 1,4-dioxane at 15℃; for 12h;	97%

1-phenylmethyl-4-piperidone (3612-20-2) → 4-piperidone hydrochloride (41979-39-9)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium dihydroxide In ethanol at 20℃; under 3102.89 Torr; for 24h;	97%

3-[3-(4-hydroxypiperidinylazo)phenoxy]propyloxymethylpolystyrene → 4-piperidone hydrochloride (41979-39-9)

Conditions	Yield
Stage #1: 3-[3-(4-hydroxypiperidinylazo)phenoxy]propyloxymethylpolystyrene With pyridine; Dess-Martin periodane In dichloromethane at 20℃; for 72h; Stage #2: With trifluoroacetic acid In dichloromethane at 0℃; Stage #3: With hydrogenchloride In dichloromethane Further stages.;	62%

4-Oxo-piperidine-3-carboximidic acid methyl ester; hydrochloride → 4-piperidone hydrochloride (41979-39-9)

Conditions	Yield
With hydrogenchloride for 0.5h; Heating;	50%

piperidine-4,4-diol hydrochloride (40064-34-4) → 4-piperidone hydrochloride (41979-39-9)

Conditions	Yield
With thionyl chloride

di-tert-butyl dicarbonate (24424-99-5) + 4-piperidone hydrochloride (41979-39-9) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With sodium hydrogencarbonate In water 1) 35 deg C, 1 h; 2) 50 deg C, 2.5 h;	100%
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 16h;	100%
Stage #1: di-tert-butyl dicarbonate; 4-piperidone hydrochloride With triethylamine; dmap In methanol at 20℃; for 20h; Stage #2: With hydrogenchloride In dichloromethane	100%

4-piperidone hydrochloride (41979-39-9) + benzyl chloroformate (501-53-1) → benzyl 4-oxo-1-piperidinecarboxylate (19099-93-5)

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water at 0 - 20℃;	100%
With sodium hydrogencarbonate In 1,4-dioxane; water at 18 - 25℃; for 48h;	100%
With sodium hydroxide In tetrahydrofuran; water at 0℃; for 1h;	99.5%

6-fluoro-1H-indole (399-51-9) + 4-piperidone hydrochloride (41979-39-9) → 6-fluoro-3-(1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indole (180161-14-2)

Conditions	Yield
With potassium hydroxide In methanol for 60h; Condensation; Heating;	100%
With potassium hydroxide In methanol at 70℃; for 5h;

4-piperidone hydrochloride (41979-39-9) + 4-methoxy-benzaldehyde (123-11-5) → (3E,5E)-3,5-bis(4′-methoxybenzylidene)-piperidin-4-one (919091-64-8)

Conditions	Yield
With hydrogenchloride; acetic acid at 20℃; for 24h;	100%
With hydrogenchloride; acetic acid
With sodium hydroxide In methanol at 20℃; for 3h; Aldol Condensation;

4-piperidone hydrochloride (41979-39-9) + methyl chloroformate (79-22-1) → 4-oxo-piperidine-1-carboxylic acid methyl ester (29976-54-3)

Conditions	Yield
Stage #1: 4-piperidone hydrochloride With potassium carbonate In tetrahydrofuran; water at 20℃; Inert atmosphere; Stage #2: methyl chloroformate In tetrahydrofuran; water at 0 - 20℃; for 2h; Inert atmosphere;	100%
With potassium carbonate In water at 0℃; for 2h;	98.7%
With potassium carbonate In water at 0℃; for 2h;	94%

4-piperidone hydrochloride (41979-39-9) + 1-(4-fluorophenyl)-N-methyl-1H-indole-5-carboxamide (330944-14-4) → 1-(4-fluorophenyl)-N-methyl-3-(1,2,3,6-tetrahydro-4-pyridyl)-1H-indole-5-carboxamide (330944-15-5)

Conditions	Yield
With trifluoroacetic acid In acetic acid for 1.5h; Heating;	100%

5-(aminooxymethyl)-2-fluorobenzonitrile hydrochloride (1002750-73-3) + 4-piperidone hydrochloride (41979-39-9) → 2-fluoro-5-((piperidin-4-ylideneaminooxy)methyl)benzonitrile (1002750-64-2)

Conditions	Yield
With sodium acetate In ethanol at 20℃; for 6h;	100%

4-piperidone hydrochloride (41979-39-9) + 4-hydrazinobenzoic acid hydrochloride (24589-77-3, 52455-33-1) → 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylic acid (929345-60-8)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 17℃; Heating / reflux;	100%
With hydrogenchloride In 1,4-dioxane for 17h; Heating / reflux;	100%
With hydrogenchloride In 1,4-dioxane for 3h; Reflux;

4-piperidone hydrochloride (41979-39-9) + trifluoroacetic anhydride (407-25-0) → 1-(trifluoroacetyl)-4-piperidone (65220-86-2)

Conditions	Yield
Stage #1: 4-piperidone hydrochloride With triethylamine In dichloromethane for 0.166667h; Stage #2: trifluoroacetic anhydride In dichloromethane at 0 - 20℃; for 2h;	100%
With triethylamine In dichloromethane Cooling with ice;	100%
With triethylamine In dichloromethane at 0 - 20℃; for 2.16667h;	100%

1,3-benzodioxol-5-ylmethyl methanesulfonate (78358-16-4) + 4-piperidone hydrochloride (41979-39-9) → 1-(benzo[d][1,3]dioxol-5-ylmethyl)piperidin-4-one (865449-49-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	100%

4-piperidone hydrochloride (41979-39-9) + 2-(trifluoromethyl)phenylhydrazine hydrochloride (3107-34-4) → 6-(trifluoromethyl)-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole (773849-01-7)

Conditions	Yield
With boron trifluoride diethyl etherate; acetic acid In ethanol for 8h; Fischer indole synthesis;	100%
Stage #1: 4-piperidone hydrochloride; 2-(trifluoromethyl)phenylhydrazine hydrochloride With boron trifluoride diethyl etherate In acetic acid at 90℃; for 8h; Stage #2: With sodium hydroxide In water pH=14;

4-piperidone hydrochloride (41979-39-9) + 3-phenoxypropyl bromide (588-63-6) → 1-(3-phenoxypropyl)piperidin-4-one (100873-41-4)

Conditions	Yield
With potassium carbonate; sodium sulfate; potassium iodide In acetonitrile for 2.5h; Reflux;	100%
With potassium carbonate In methanol at 20 - 60℃;

4-piperidone hydrochloride (41979-39-9) + 1,3-bis-(bromomethyl)benzene (626-15-3) → 1,1'-(1,3-phenylenebis(methylene))bis(piperidin-4-one) (1359979-28-4)

Conditions	Yield
With potassium carbonate In methanol; dichloromethane at 20℃; for 48h;	100%
With sodium carbonate In acetonitrile at 60℃; Sonication;	72%

1-[2-(methylsulfanyl)phenyl]hydrazine (88965-67-7) + 4-piperidone hydrochloride (41979-39-9) → 6-(methylsulphide)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (764648-07-9)

Conditions	Yield
With hydrogenchloride In ethanol; water at 80℃; Fischer indole synthesis;	100%

4-piperidone hydrochloride (41979-39-9) + (2-iodophenyl)hydrazine hydrochloride (60481-34-7) → 6-iodo-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (717843-40-8)

Conditions	Yield
With hydrogenchloride In ethanol; water Fischer indole synthesis;	100%

4-piperidone hydrochloride (41979-39-9) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 1-(2-amino-4-chlorobenzoyl)piperidin-4-one (1451261-87-2)

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;	100%

4-piperidone hydrochloride (41979-39-9) + 4-(methylsulfonyl)phenylhydrazine hydrochloride (17852-67-4) → 8-methylsulfonyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride

Conditions	Yield
Stage #1: 4-piperidone hydrochloride; 4-(methylsulfonyl)phenylhydrazine hydrochloride In ethanol at 20℃; for 0.5h; Stage #2: With boron trifluoride diethyl etherate; acetic acid at 90℃; for 16h;	100%

4-piperidone hydrochloride (41979-39-9) + 4-(methylsulfonyl)phenylhydrazine hydrochloride (17852-67-4) → 8-(methylsulfonyl)-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl

Conditions	Yield
Stage #1: 4-piperidone hydrochloride; 4-(methylsulfonyl)phenylhydrazine hydrochloride In ethanol at 20℃; for 0.5h; Fischer Indole Synthesis; Stage #2: With boron trifluoride diethyl etherate; acetic acid at 90℃; for 16h; Fischer Indole Synthesis;	100%

4-piperidone hydrochloride (41979-39-9) + methanesulfonyl chloride (124-63-0) → 1-(methylsulfonyl)piperidin-4-one (218780-53-1)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 20 - 32℃; for 2h;	99.7%
With potassium carbonate In chloroform; water at 0 - 20℃; for 73h;	87%
With potassium carbonate In chloroform; water at 0 - 20℃; for 73h;	87%

4-piperidone hydrochloride (41979-39-9) + 5-({[1-(4-Chloro-phenyl)-methanoyl]-amino}-methyl)-thiophene-2-sulfonyl chloride (166964-34-7) → 4-Chloro-N-({5-[(4-oxopiperidin-1-yl)sulfonyl]thien-2-yl}methyl)benzamide

Conditions	Yield
With sodium hydroxide In chloroform; water for 15h;	99.5%

4-piperidone hydrochloride (41979-39-9) + p-toluenesulfonyl chloride (98-59-9) → N-tosyl-4-piperidone (33439-27-9)

Conditions	Yield
With potassium carbonate Inert atmosphere;	99%
With magnesium(II) perchlorate In chloroform; water at 20℃; for 10h;	95%
With potassium carbonate In dichloromethane; water at 20℃; for 16h;	95%

4-piperidone hydrochloride (41979-39-9) + benzene (71-43-2) → 4,4-diphenylpiperidine (34273-01-3)

Conditions	Yield
With trifluorormethanesulfonic acid at 20℃; for 3h; Substitution;	99%
With trifluorormethanesulfonic acid at 20℃; for 24h;

4-piperidone hydrochloride (41979-39-9) + 4-chlorobenzenesulfonyl chloride (98-60-2) → 1-(4-chloro-benzenesulfonyl)-piperidin-4-one (156634-92-3)

Conditions	Yield
With potassium carbonate In chloroform; water at 20℃;	99%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + 4-piperidone hydrochloride (41979-39-9) → C19H26N2O4 (1198179-29-1)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	99%

3,4-dibromo-1-methyl-2,5-dihydropyrrole-2,5-dione (3005-27-4) + 4-piperidone hydrochloride (41979-39-9) → 3-bromo-1-methyl-4-(4-oxopiperidin-1-yl)-1H-pyrrole-2,5-dione (1202376-63-3)

Conditions	Yield
With potassium carbonate In acetonitrile for 2h; Reflux;	99%

1-chloro-4-(chloromethyl)-2-methylbenzene (92304-76-2) + 4-piperidone hydrochloride (41979-39-9) → 1-(4-chloro-3-methyl-benzyl)-piperidin-4-one (1251529-07-3)

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water; N,N-dimethyl-formamide at 50 - 70℃; for 7h; Large scale;	99%
With potassium carbonate In tetrahydrofuran; water; N,N-dimethyl-formamide at 70℃; for 7h; Large scale;	99%

4-piperidone hydrochloride (41979-39-9) + N-tert-butoxycarbonyl-O-2,6-dichlorobenzyl-L-tyrosine (40298-71-3) → 1-[N-tert-butoxycarbonyl-O-(2,6-dichlorobenzyl)-L-tyrosyl]-piperidin-4-one (1070383-27-5)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃;	98.8%

tert-butyl carbamate (4248-19-5) + 4-piperidone hydrochloride (41979-39-9) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
Stage #1: 4-piperidone hydrochloride With sodium hydroxide In water at 0℃; Stage #2: tert-butyl carbazate In water for 4h;	98.44%

4-piperidone hydrochloride (41979-39-9) + chloroformic acid ethyl ester (541-41-3) → N-ethoxycarbonyl-4-piperidone (29976-53-2)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;	98%
With triethylamine In dichloromethane at 0 - 20℃; for 2h;	98%
With sodium hydroxide In diethyl ether; water at 0℃; for 0.166667h;	93%

Upstream product

• 3612-20-2 1-phenylmethyl-4-piperidone 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 40064-34-4 piperidine-4,4-diol hydrochloride 

Downstream Products

• 141945-71-3 1-(thien-2-oyl)-4-oxopiperidine 
• 134348-51-9 1-(4-Fluorobenzyl)-4-piperidone 
• 186908-24-7 Acetic acid 4-(4-oxo-piperidine-1-carbonyl)-phenyl ester 
• 216983-38-9 1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-one 
• 220772-52-1 1-(3,4-dichlorobenzyl)-4-piperidone 
• 267666-08-0 1-(benzylsulfonyl)piperidin-4-one 
• 180161-14-2 6-fluoro-3-(1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indole 
• 3612-20-2 1-phenylmethyl-4-piperidone 
• 919091-62-6 (3E,5E)-3,5-bis(4-fluorobenzylidene)piperidin-4-one 
• 919091-60-4 (3E,5E)-3,5-bis(4-chlorobenzylidene)-4-piperidone 
• 919091-63-7 (3E,5E)-3,5-bis[(4-nitrophenyl)methylidene]piperidin-4-one 
• 132766-61-1 3,5-dibenzylidenepiperidin-4-one 
• 919091-64-8 (3E,5E)-3,5-bis(4′-methoxybenzylidene)-piperidin-4-one 
• 145888-79-5 3,5-bis((E)-3,4-dichlorobenzylidene)-4-oxopiperidin 

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