25519-80-6

Basic information

• Product Name: 4-BENZOYLPIPERIDINE HYDROCHLORIDE
• Synonyms: PHENYL-PIPERIDIN-4-YL-METHANONE HYDROCHLORIDE;PHENYL(4-PIPERIDYL)METHANONE HYDROCHLORIDE;PHENYL(4-PIPERIDINYL)METHANONE;TIMTEC-BB SBB003319;4-BENZOYL PIPERIDINE HCL;phenyl(4-piperidyl)methanoneHCl;4-Benzoylpiperidine hydrochloride,98%;Phenyl 4-Piperidyl Ketone Hydrochloride
• CAS NO: 25519-80-6
• Molecular Formula: C₁₂H₁₅NO*ClH
• Molecular Weight: 225.71
• Product Categories: Pyrans, Piperidines & Piperazines;Aromatics;Heterocycles;Neurochemicals
• Mol File: 25519-80-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 95-97°C
• Boiling Point: 310.7°Cat760mmHg
• Flash Point: 125.3°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 0.000589mmHg at 25°C
• Storage Temp.: -20?C Freezer
• Stability: Store in Freezer at -20°C
• CAS DataBase Reference: 4-BENZOYLPIPERIDINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZOYLPIPERIDINE HYDROCHLORIDE(25519-80-6)
• EPA Substance Registry System: 4-BENZOYLPIPERIDINE HYDROCHLORIDE(25519-80-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37
• Hazardous Substances Data: 25519-80-6(Hazardous Substances Data)

Usage

Description

4-Benzoylpiperidine hydrochloride is a synthetic intermediate that is used in the preparation of CNS depressants. It is a white to almost white powder in its chemical form.

Uses

Used in Pharmaceutical Industry:
4-Benzoylpiperidine hydrochloride is used as a synthetic intermediate for the production of central nervous system (CNS) depressants. It plays a crucial role in the development of medications that help in reducing the activity of the CNS, leading to a calming or sedating effect.
The applications of 4-Benzoylpiperidine hydrochloride in the pharmaceutical industry are primarily focused on its use in the synthesis of various CNS depressants, which are essential for treating a range of conditions, including anxiety, insomnia, and certain neurological disorders.

InChI:InChI=1/C12H15NO/c14-12(10-4-2-1-3-5-10)11-6-8-13-9-7-11/h1-5,11,13H,6-9H2/p+1

Synthetic route

1-(t-butoxycarbonyl)-4-(benzoyl)piperidine (193217-39-9) → 4-(benzoyl)piperidine hydrochloride (25519-80-6)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 18 - 25℃; for 0.5h;	98%
With hydrogenchloride In 1,4-dioxane

1-(4-benzoylpiperidin-1-yl)ethanone (25519-79-3) → 4-(benzoyl)piperidine hydrochloride (25519-80-6)

Conditions	Yield
With hydrogenchloride; water In tetrahydrofuran for 10h; Reflux;

1-acetyl-piperidine-4-carboxylic acid (25503-90-6) → 4-(benzoyl)piperidine hydrochloride (25519-80-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride; N,N-dimethyl-formamide / 1,2-dichloro-ethane / 4 h / 0 - 60 °C 2: aluminum (III) chloride / 1,2-dichloro-ethane / 16 h / 0 - 65 °C 3: hydrogenchloride; water / tetrahydrofuran / 10 h / Reflux View Scheme

isonipecotic acid (498-94-2) → 4-(benzoyl)piperidine hydrochloride (25519-80-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / 2 h / 140 °C 2: thionyl chloride; N,N-dimethyl-formamide / 1,2-dichloro-ethane / 4 h / 0 - 60 °C 3: aluminum (III) chloride / 1,2-dichloro-ethane / 16 h / 0 - 65 °C 4: hydrogenchloride; water / tetrahydrofuran / 10 h / Reflux View Scheme

1-acetylpiperidine-4-carbonyl chloride (59084-16-1) → 4-(benzoyl)piperidine hydrochloride (25519-80-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 1,2-dichloro-ethane / 16 h / 0 - 65 °C 2: hydrogenchloride; water / tetrahydrofuran / 10 h / Reflux View Scheme

benzyl chloroformate (501-53-1) + 4-(benzoyl)piperidine hydrochloride (25519-80-6) → 4-benzoylpiperidine-1-carboxylic acid benzyl ester (922504-27-6)

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 0 - 20℃; for 2h;	100%
With potassium carbonate In tetrahydrofuran at 0 - 25℃; for 15h; Inert atmosphere;	97.76%
With potassium carbonate In tetrahydrofuran at 0 - 20℃; for 2h;	90%
With potassium carbonate In 1,4-dioxane; water Cooling with ice;	1.43 g

di-tert-butyl dicarbonate (24424-99-5) + 4-(benzoyl)piperidine hydrochloride (25519-80-6) → 1-(t-butoxycarbonyl)-4-(benzoyl)piperidine (193217-39-9)

Conditions	Yield
With potassium hydrogencarbonate In tetrahydrofuran; water for 1h; Condensation; Heating;	98%
With sodium carbonate In tetrahydrofuran; water for 1h; Heating;	98%
With potassium hydrogencarbonate In H2 O-TBF	98%

4-(benzoyl)piperidine hydrochloride (25519-80-6) + 1-methyl-1H-imidazole-4-sulfonyl chloride (137049-00-4) → (1-(1-Methyl-1H-Imidazol-4-ylsulfonyl)Piperidin-4-yl)(Phenyl)Methanone (1246526-78-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 18h;	93%

2-(benzylthio)-4-(4-methoxyphenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile (138608-95-4) + 4-(benzoyl)piperidine hydrochloride (25519-80-6) → C31H28N4O2S (1425974-12-4)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 12h;	70%

4-(benzoyl)piperidine hydrochloride (25519-80-6) + 2-Benzylsulfanyl-4-(4-chloro-phenyl)-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile → C30H25ClN4OS (1425974-03-3)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 12h;	64%

4-(benzoyl)piperidine hydrochloride (25519-80-6) + 1-(4-Chlorobutyl)-7-methyl-6,7-dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)-dione (136975-57-0) → 1-[4-(4-benzoyl-piperidin-1-yl)-butyl]-7-methyl-6,7-dihydro-1H,5H-pyrrolo[2,3-c]azepine-4,8-dione

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h;	61%

1,1-dimethylethyl[trans-4-(2-oxoethyl)cyclohexyl]carbamate (215790-29-7) + 4-(benzoyl)piperidine hydrochloride (25519-80-6) → {trans-4-[2-(4-benzoyl-piperidin-1-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester

Conditions	Yield
Stage #1: 1,1-dimethylethyl[trans-4-(2-oxoethyl)cyclohexyl]carbamate; 4-(benzoyl)piperidine hydrochloride With acetic acid In 1,2-dichloro-ethane at 20℃; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane Stage #3: With water; sodium hydrogencarbonate In 1,2-dichloro-ethane	49%

3-(benzyloxy)-6-bromo-2,4,5-trimethylpyridine (1444336-77-9) + 4-(benzoyl)piperidine hydrochloride (25519-80-6) → (1-(5-(benzyloxy)-3,4,6-trimethylpyridin-2-yl)piperidin-4-yl)(phenyl)methanone

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 130℃; for 24h;	27%

4-(benzoyl)piperidine hydrochloride (25519-80-6) + benzenesulfenyl chloride (931-59-9) → 4-benzoylpiperidine-1-benzenesulfenamide (74129-96-7)

Conditions	Yield
With triethylamine In dichloromethane for 2.5h; Ambient temperature;	13.2%

4-(benzoyl)piperidine hydrochloride (25519-80-6) + 1-(4-tert-Butyl-phenyl)-4-iodo-butan-1-one → 4-(4-benzoylpiperidin-1-yl)-1-<4-(1,1-dimethylethyl)phenyl>-1-butanone (151091-52-0)

Conditions	Yield
With potassium carbonate In acetone Heating; Yield given;

4-(benzoyl)piperidine hydrochloride (25519-80-6) → tert-butyl (S)-4-(hydroxy(phenyl)methyl)piperidine-1-carboxylate

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / sodium carbonate / H2O; tetrahydrofuran / 1 h / 80 °C 2: formic acid; triethylamine / [((S,S)-N-(1,2,6-triphenyl-3-azahexyl)tosylamido)RuCl] / 16 h / 40 °C View Scheme

4-(benzoyl)piperidine hydrochloride (25519-80-6) → tert-butyl (R)-4-(hydroxy(phenyl)methyl)piperidine-1-carboxylate

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / sodium carbonate / H2O; tetrahydrofuran / 1 h / 80 °C 2: formic acid; triethylamine / [((S,S)-N-(1,2,6-triphenyl-3-azahexyl)tosylamido)RuCl] / 16 h / 40 °C View Scheme

4-(benzoyl)piperidine hydrochloride (25519-80-6) → 4-(hydroxyphenylmethyl)piperidine-1-carboxylic acid tert-butyl ester (269740-46-7, 269741-35-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / sodium carbonate / H2O; tetrahydrofuran / 1 h / 80 °C 2: sodium borohydride View Scheme

4-(benzoyl)piperidine hydrochloride (25519-80-6) → N,N-diethyl-4-(phenyl-piperidin-4-yl-methyl)-benzamide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 98 percent / KHCO3 / tetrahydrofuran; H2O / 1 h / Heating 2.1: t-BuLi / tetrahydrofuran; hexane / -78 °C 2.2: 94 percent / tetrahydrofuran; hexane / -78 - 20 °C 3.1: 82 percent / Et3SiH; TFA / CH2Cl2 / 72 h / 25 °C View Scheme

4-(benzoyl)piperidine hydrochloride (25519-80-6) → AR-M390 (209808-01-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 98 percent / Na2CO3 / tetrahydrofuran; H2O / 1 h / Heating 2.1: t-BuLi / tetrahydrofuran / 0.17 h / -78 °C 2.2: 94 percent / tetrahydrofuran / -78 - 20 °C 3.1: 91 percent / TFA / CH2Cl2 / 20 °C View Scheme

4-(benzoyl)piperidine hydrochloride (25519-80-6) → N,N-Diethyl-4-[(1-methyl-piperidin-4-ylidene)-phenyl-methyl]-benzamide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 98 percent / Na2CO3 / tetrahydrofuran; H2O / 1 h / Heating 2.1: t-BuLi / tetrahydrofuran / 0.17 h / -78 °C 2.2: 94 percent / tetrahydrofuran / -78 - 20 °C 3.1: 91 percent / TFA / CH2Cl2 / 20 °C 4.1: 48 mg / K2CO3 / acetonitrile / 0.5 h / 25 °C View Scheme

4-(benzoyl)piperidine hydrochloride (25519-80-6) → N,N-Diethyl-4-(phenyl-N-allyl-piperidin-4-ylidene-methyl)-benzamide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 98 percent / Na2CO3 / tetrahydrofuran; H2O / 1 h / Heating 2.1: t-BuLi / tetrahydrofuran / 0.17 h / -78 °C 2.2: 94 percent / tetrahydrofuran / -78 - 20 °C 3.1: 91 percent / TFA / CH2Cl2 / 20 °C 4.1: 86 percent / K2CO3 / acetonitrile / 0.5 h / 25 °C View Scheme

4-(benzoyl)piperidine hydrochloride (25519-80-6) → N,N-diethyl-4-[phenyl-(1-phenyl-piperidin-4-ylidene)-methyl]-benzamide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 98 percent / Na2CO3 / tetrahydrofuran; H2O / 1 h / Heating 2.1: t-BuLi / tetrahydrofuran / 0.17 h / -78 °C 2.2: 94 percent / tetrahydrofuran / -78 - 20 °C 3.1: 91 percent / TFA / CH2Cl2 / 20 °C 4.1: 56 percent / Pd(dba)2; BINAP; sodium tert-butoxide / toluene / 12 h / 80 - 90 °C View Scheme

4-(benzoyl)piperidine hydrochloride (25519-80-6) → 4-[(1-cyclopropylmethyl-piperidin-4-ylidene)-phenyl-methyl]-N,N-diethyl-benzamide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 98 percent / Na2CO3 / tetrahydrofuran; H2O / 1 h / Heating 2.1: t-BuLi / tetrahydrofuran / 0.17 h / -78 °C 2.2: 94 percent / tetrahydrofuran / -78 - 20 °C 3.1: 91 percent / TFA / CH2Cl2 / 20 °C 4.1: 86 percent / K2CO3 / acetonitrile / 0.5 h / 25 °C View Scheme

4-(benzoyl)piperidine hydrochloride (25519-80-6) → 4-[(1-butyl-piperidin-4-ylidene)-phenyl-methyl]-N,N-diethyl-benzamide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 98 percent / Na2CO3 / tetrahydrofuran; H2O / 1 h / Heating 2.1: t-BuLi / tetrahydrofuran / 0.17 h / -78 °C 2.2: 94 percent / tetrahydrofuran / -78 - 20 °C 3.1: 91 percent / TFA / CH2Cl2 / 20 °C 4.1: 85 percent / K2CO3 / acetonitrile / 0.5 h / 25 °C View Scheme

4-(benzoyl)piperidine hydrochloride (25519-80-6) → N,N-Diethyl-4-[(N-3-methyl-2-butenyl)-phenyl-piperidin-4-ylidene-methyl]-benzamide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 98 percent / Na2CO3 / tetrahydrofuran; H2O / 1 h / Heating 2.1: t-BuLi / tetrahydrofuran / 0.17 h / -78 °C 2.2: 94 percent / tetrahydrofuran / -78 - 20 °C 3.1: 91 percent / TFA / CH2Cl2 / 20 °C 4.1: 71 percent / K2CO3 / acetonitrile / 0.5 h / 25 °C View Scheme

4-(benzoyl)piperidine hydrochloride (25519-80-6) → 4-(α-hydroxy-α-(4-N-tert-butoxycarbonylpiperidinyl)benzyl)-N,N-diethylbenzamide (193217-40-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 98 percent / KHCO3 / tetrahydrofuran; H2O / 1 h / Heating 2.1: t-BuLi / tetrahydrofuran; hexane / -78 °C 2.2: 94 percent / tetrahydrofuran; hexane / -78 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: 98 percent / Na2CO3 / tetrahydrofuran; H2O / 1 h / Heating 2.1: t-BuLi / tetrahydrofuran / 0.17 h / -78 °C 2.2: 94 percent / tetrahydrofuran / -78 - 20 °C View Scheme

4-(benzoyl)piperidine hydrochloride (25519-80-6) → 4-[(1-cyclohexyl-piperidin-4-ylidene)-phenyl-methyl]-N,N-diethyl-benzamide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 98 percent / Na2CO3 / tetrahydrofuran; H2O / 1 h / Heating 2.1: t-BuLi / tetrahydrofuran / 0.17 h / -78 °C 2.2: 94 percent / tetrahydrofuran / -78 - 20 °C 3.1: 91 percent / TFA / CH2Cl2 / 20 °C 4.1: Ti(OPr-i)4 / 20 °C / microwave irradiation 4.2: 20 percent / NaBH4 / ethanol / 12 h / 20 °C View Scheme

4-(benzoyl)piperidine hydrochloride (25519-80-6) → 1-<4-<4-(1,1-dimethylethyl)phenyl>-4-hydroxybutyl>-α-phenyl-4-piperidinomethanol

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / acetone / Heating 2: 98 percent / NaBH4 / methanol / 2 h / Ambient temperature View Scheme

methanesulfonyl chloride (124-63-0) + 4-(benzoyl)piperidine hydrochloride (25519-80-6) → 4-benzoyl-1-methanesulphonylpiperidine (515154-31-1)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 25℃; for 16h;
With triethylamine In dichloromethane at 0 - 20℃; for 16h;
With triethylamine In dichloromethane at 0 - 20℃; for 16h;
With triethylamine In dichloromethane at 0 - 20℃; for 16h;
With triethylamine In dichloromethane at 0 - 20℃; for 16h;

4-(benzoyl)piperidine hydrochloride (25519-80-6) + trifluoroacetic anhydride (407-25-0) → 4-(2-nitrobenzoyl)-1-trifluoromethylcarbonylpiperidine + N-trifluoroacetyl-4-(m-nitrobenzoyl)piperidine + N-trifluoroacetyl-4-(p-nitrobenzoyl)piperidine

Conditions	Yield
Stage #1: 4-(benzoyl)piperidine hydrochloride; trifluoroacetic anhydride at 20℃; for 21h; Heating / reflux; Stage #2: With ammonium nitrate In trifluoroacetic anhydride at 5 - 10℃; for 1.75h;
Stage #1: 4-(benzoyl)piperidine hydrochloride; trifluoroacetic anhydride at 20℃; for 27h; Heating / reflux; Stage #2: With nitric acid In trifluoroacetic anhydride at 5 - 10℃; for 1.33333h;

4-(benzoyl)piperidine hydrochloride (25519-80-6) + phenylmagnesium bromide (100-58-3) → 4-(diphenylmethylene)piperidine (50706-57-5)

Conditions	Yield
Stage #1: 4-(benzoyl)piperidine hydrochloride; phenylmagnesium bromide In tetrahydrofuran at 20℃; for 12h; Stage #2: With trifluoroacetic acid for 12h; Stage #3: With sodium hydrogencarbonate In water; ethyl acetate

intermediate 4 (625099-22-1) + 4-(benzoyl)piperidine hydrochloride (25519-80-6) → C30H36F3N3O2 + C30H36F3N3O2 + C30H36F3N3O2 + C30H36F3N3O2

Conditions	Yield
Stage #1: intermediate 4; 4-(benzoyl)piperidine hydrochloride With sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine In dichloromethane Molecular sieve; Stage #2: With water; sodium hydrogencarbonate In dichloromethane
Stage #1: intermediate 4; 4-(benzoyl)piperidine hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane for 16h;

4-(benzoyl)piperidine hydrochloride (25519-80-6) + 1,3-chlorobromopropane (109-70-6) → (1-(3-chloropropyl)piperidin-4-yl)(phenyl)methanone (106134-85-4)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogen sulfate In water; toluene

Upstream product

• 193217-39-9 1-(t-butoxycarbonyl)-4-(benzoyl)piperidine 
• 25519-79-3 1-(4-benzoylpiperidin-1-yl)ethanone 
• 25503-90-6 1-acetyl-piperidine-4-carboxylic acid 
• 498-94-2 isonipecotic acid 
• 59084-16-1 1-acetylpiperidine-4-carbonyl chloride 

Downstream Products

• 151091-52-0 4-(4-benzoylpiperidin-1-yl)-1-<4-(1,1-dimethylethyl)phenyl>-1-butanone 
• 74129-96-7 4-benzoylpiperidine-1-benzenesulfenamide 
• 193217-39-9 1-(t-butoxycarbonyl)-4-(benzoyl)piperidine 
• 269740-46-7 4-(hydroxyphenylmethyl)piperidine-1-carboxylic acid tert-butyl ester 
• 209808-01-5 AR-M390 
• 193217-40-2 4-(α-hydroxy-α-(4-N-tert-butoxycarbonylpiperidinyl)benzyl)-N,N-diethylbenzamide 
• 515154-31-1 4-benzoyl-1-methanesulphonylpiperidine 
• 50706-57-5 4-(diphenylmethylene)piperidine 

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