10315-03-4

Basic information

• Product Name: 4-ACETYL-4-PHENYLPIPERIDINE HYDROCHLORIDE
• Synonyms: TIMTEC-BB SBB003218;1-(4-phenylpiperidin-4-yl)ethan-1-one hydrochloride;4-ACETYL-4-PHENYLPIPERIDINE HYDROCHLORIDE 99%;4-Acetyl-4-phenylpiperidine hydrochloride,99%;1-(4-Phenylpiperidin-4-yl)ethanone hydrochloride;1-(4-Phenyl-4-piperidinyl)-ethanone hydrochloride;4-ACETYL-4-PHENYLPIPERIDINE HCL;4-ACETYL-4-PHENYLPIPERIDINE HYDROCHLORIDE
• CAS NO: 10315-03-4
• Molecular Formula: C₁₃H₁₇NO*ClH
• Molecular Weight: 239.74
• EINECS: 233-694-0
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Piperidines
• Mol File: 10315-03-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 232-234 °C(lit.)
• Boiling Point: 325.2 °C at 760 mmHg
• Flash Point: 125.7 °C
• Appearance: Slightly yellow to beige/Powder
• Vapor Pressure: 0.000234mmHg at 25°C
• Solubility: water: soluble(lit.)
• Water Solubility: almost transparency
• CAS DataBase Reference: 4-ACETYL-4-PHENYLPIPERIDINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ACETYL-4-PHENYLPIPERIDINE HYDROCHLORIDE(10315-03-4)
• EPA Substance Registry System: 4-ACETYL-4-PHENYLPIPERIDINE HYDROCHLORIDE(10315-03-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 10315-03-4(Hazardous Substances Data)

Usage

Chemical Properties

slightly yellow to beige powder

Uses

Reactant for synthesis of neurotransmitter transport inhibitors with activity at dopamine receptor sites

General Description

4-Acetyl-4-phenylpiperidine hydrochloride generates acetylperoxyl radical via laser flash photolysis in the presence of oxygen.

InChI:InChI=1/C13H17NO/c1-11(15)13(7-9-14-10-8-13)12-5-3-2-4-6-12/h2-6,14H,7-10H2,1H3/p+1

Synthetic route

1-(1-benzyl-4-phenyl-[4]piperidyl)-ethanone; hydrochloride (10315-02-3) → 4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4)

Conditions	Yield
With hydrogenchloride; palladium on activated charcoal Hydration;

1,4-diacetyl 4-phenyl piperidine → 4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4)

Conditions	Yield
Stage #1: 1,4-diacetyl 4-phenyl piperidine With water; sodium hydroxide In methanol at 20℃; for 10h; Stage #2: With hydrogenchloride In methanol; water pH=2;	800 mg

p-phenylpyridine (939-23-1) → 4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: indium / 7 h / 95 - 100 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 60 °C / Autoclave 3.1: sodium hydroxide; water / methanol / 10 h / 20 °C 3.2: pH 2 View Scheme

1,4-diacetyl 4-phenyl 1,4-dihydropyridine (41225-59-6) → 4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 60 °C / Autoclave 2.1: sodium hydroxide; water / methanol / 10 h / 20 °C 2.2: pH 2 View Scheme

n-propanesulfonyl chloride (10147-36-1) + 4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4) → 4-acetyl-4-phenyl-1-(propylsulfonyl)piperidine (852029-77-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 2h;	95%

4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4) + 4-Phenylbutyric acid (1821-12-1) → 1-(4-acetyl-4-phenylpiperidin-1-yl)-4-phenylbutan-1-one

Conditions	Yield
Stage #1: 4-Phenylbutyric acid With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 0.166667h; Stage #2: 4-Acetyl-4-phenylpiperidine hydrochloride In DMF (N,N-dimethyl-formamide) for 2h;	93%

1-(2-bromoethoxy)-4-methoxybenzene (22921-76-2) + 4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4) + potassium carbonate (584-08-7) → 4-acetyl-1-(2-(4-methoxyphenoxy)ethyl)-4-phenylpiperidine (193357-72-1)

Conditions	Yield
In acetonitrile	88%

4-cyclohexylbenzoic acid (20029-52-1) + 4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4) → 1-[1-(4-cyclohexylbenzoyl)-4-phenylpiperidin-4-yl]ethanone

Conditions	Yield
Stage #1: 4-cyclohexylbenzoic acid With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 0.166667h; Stage #2: 4-Acetyl-4-phenylpiperidine hydrochloride In DMF (N,N-dimethyl-formamide) for 3h;	87%

di-tert-butyl dicarbonate (24424-99-5) + 4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4) → tert-butyl 4-acetyl-4-phenylpiperidine-1-carboxylate (160376-88-5)

Conditions	Yield
With triethylamine In dichloromethane for 2h;	85%

C29H25F6N3O5*ClH + 4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4) → (3R*,4R*)-1-[(4-acetyl-4-phenylpiperidin-1-yl)carbonyl]-N-[3,5-bis(trifluoromethyl)benzyl]-N-methyl-3-phenylpiperidine-4-carboxamide

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 2h;	78%

C24H19BrCl2F6N2O2 + 4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4) → 1-[[4-(acetylamino)-4-phenylpiperidin-1-yl]acetyl]-N-[3,5-bis(trifluoromethyl)benzyl]-5-(3,4-dichlorophenyl)-N-methyl-1,2,3,6-tetrahydropyridine-4-carboxamide hydrochloride

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 14h;

4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4) → 4-(2-Bromoacetyl)-4-phenylpiperidine hydrobromide (10315-15-8)

Conditions	Yield
With bromine In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran

2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid (378758-70-4) + 4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4) → 1-(4-acetyl-4-phenyl-piperidin-1-yl)-2-(4-chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-ethanone

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In acetonitrile

1-(2-bromoethoxy)-4-methoxybenzene (22921-76-2) + 4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4) → 4-Acetyl-1-(2-(4-hydroxyphenoxy)ethyl)-4-phenylpiperidine hydrochloride (193355-80-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetonitrile 2: boron tribromide / dichloromethane View Scheme

4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4) → {1-[4-phenyl-1-(propylsulfonyl)piperidin-4-yl]ethyl}amine (936101-93-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C 2: hydroxylamine hydrochloride / pyridine / 90 °C 3: ammonia; hydrogen; nickel / methanol / 48 h / 20 °C / 2844.39 Torr View Scheme

4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4) → {(1S)-1-[4-phenyl-1-(propylsulfonyl)piperidin-4-yl]ethyl}amine (852029-79-9) + {(1R)-1-[4-phenyl-1-(propylsulfonyl)piperidin-4-yl]ethyl}amine (936101-94-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C 2: hydroxylamine hydrochloride / pyridine / 90 °C 3: ammonia; hydrogen; nickel / methanol / 48 h / 20 °C / 2844.39 Torr 4: Resolution of racemate View Scheme

4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4) → (1E)-1-[4-phenyl-1-(propylsulfonyl)piperidin-4-yl]ethanone oxime (852029-78-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C 2: hydroxylamine hydrochloride / pyridine / 90 °C View Scheme

4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4) → 2-amino-6-chloro-N-((4-phenyl-1-(propylsulfonyl)piperidin-4-yl)methyl)benzamide (852029-50-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C 2: hydroxylamine hydrochloride / pyridine / 90 °C 3: ammonia; hydrogen; nickel / methanol / 48 h / 20 °C / 2844.39 Torr 4: Resolution of racemate 5: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide / dichloromethane / 20 °C View Scheme

4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4) → N-{(1S)-1-[4-phenyl-1-(propylsulfonyl)piperidin-4-yl]ethyl}-2-(trifluoromethoxy)benzamide (852029-44-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C 2: hydroxylamine hydrochloride / pyridine / 90 °C 3: ammonia; hydrogen; nickel / methanol / 48 h / 20 °C / 2844.39 Torr 4: Resolution of racemate 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C View Scheme

4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4) → C13H16ClNO

Conditions	Yield
With N-chloro-succinimide; N-ethyl-N,N-diisopropylamine at 20℃; for 0.5h;

4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4) → C19H21NO

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; N-chloro-succinimide / 0.5 h / 20 °C 2: tris(2,2'-bipyridyl)ruthenium dichloride; perchloric acid / 1 h / 20 °C / Irradiation View Scheme

4-Acetyl-4-phenylpiperidine hydrochloride (10315-03-4) → C31H40N2O2

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; N-chloro-succinimide / 0.5 h / 20 °C 2: tris(2,2'-bipyridyl)ruthenium dichloride; perchloric acid / 1 h / 20 °C / Irradiation View Scheme

Upstream product

• 10315-02-3 1-(1-benzyl-4-phenyl-[4]piperidyl)-ethanone; hydrochloride 
• 41225-59-6 1,4-diacetyl-1,4-dihydro-4-phenylpyridine 
• 939-23-1 p-phenylpyridine 

Downstream Products

• 34798-80-6 4-acetyl-4-phenylpiperidine 
• 193357-72-1 4-acetyl-1-(2-(4-methoxyphenoxy)ethyl)-4-phenylpiperidine 
• 852029-79-9 {(1S)-1-[4-phenyl-1-(propylsulfonyl)piperidin-4-yl]ethyl}amine 
• 936101-94-9 {(1R)-1-[4-phenyl-1-(propylsulfonyl)piperidin-4-yl]ethyl}amine 
• 22940-55-2 1-(4-phenyl-1-tosylpiperidin-4-yl)ethan-1-one 
• 193355-80-5 4-Acetyl-1-(2-(4-hydroxyphenoxy)ethyl)-4-phenylpiperidine hydrochloride 
• 852029-77-7 4-acetyl-4-phenyl-1-(propylsulfonyl)piperidine 
• 10315-15-8 4-(2-Bromoacetyl)-4-phenylpiperidine hydrobromide 

Relevant articles and documents

Synthesis of 4-aryl 4-acyl piperidine, its salts and analogs using indium metal

A novel process for the synthesis of 4-aryl 4-acyl piperidine derivatives using indium metal is described. Specifically, a novel process for the synthesis of 4-acetyl 4-phenyl piperidine and its salts using indium metal is described.