23056-29-3

Basic information

• Product Name: N-phenylpiperidin-4-amine
• Synonyms: N-phenylpiperidin-4-amine;Phenyl-Piperidine-4-YL-Amine;n-Phenyl-4-piperidinamine, 98%;Despropionyl norfentanyl;N-Phenyl-4-piperidinamine,98%;phenyl(4-piperidyl)amine;4-Piperidinamine,N-phenyl-;Fentanyl Related Compound B (10 mg) (4-Anilinopiperidine)
• CAS NO: 23056-29-3
• Molecular Formula: C₁₁H₁₆N₂
• Molecular Weight: 176.25814
• EINECS: 245-402-9
• Product Categories: pharmaceutical
• Mol File: 23056-29-3.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 312°Cat760mmHg
• Flash Point: 185.3°C
• Appearance: /
• Density: 1.052g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.579
• PKA: 9.83±0.10(Predicted)
• CAS DataBase Reference: N-phenylpiperidin-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-phenylpiperidin-4-amine(23056-29-3)
• EPA Substance Registry System: N-phenylpiperidin-4-amine(23056-29-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 23056-29-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H16N2/c1-2-4-10(5-3-1)13-11-6-8-12-9-7-11/h1-5,11-13H,6-9H2

Synthetic route

1-(tert-butoxycarbonyl)-4-phenylaminopiperidine (125541-22-2) → phenyl-piperidin-4-yl-amine (23056-29-3)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 1h;	100%
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 3h;	86%
With trifluoroacetic acid In dichloromethane

N-(1-ethoxycarbonyl-4-piperidinyl)aniline (116512-92-6) → phenyl-piperidin-4-yl-amine (23056-29-3)

Conditions	Yield
With hydrogenchloride In water for 16h; Heating;	92%

4-aminopiperidine (13035-19-3) + chlorobenzene (108-90-7) → 1-phenylpiperidin-4-ylamine (63921-23-3) + 1-phenyl-4-(phenylamino)piperidine + phenyl-piperidin-4-yl-amine (23056-29-3)

Conditions	Yield
With sodium t-butanolate; DavePhos; tris-(dibenzylideneacetone)dipalladium(0) In xylene at 130℃; for 24h;	A 60% B 7% C n/a

4-aminopiperidine (13035-19-3) + bromobenzene (108-86-1) → 1-phenylpiperidin-4-ylamine (63921-23-3) + 1-phenyl-4-(phenylamino)piperidine + phenyl-piperidin-4-yl-amine (23056-29-3)

Conditions	Yield
With chiral ferrocene; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In xylene at 130℃; for 24h; Product distribution; Further Variations:; Reagents;	A 18% B 8% C 15%

aniline (62-53-3) + ethane-α.β-bis-sulfonic acid chloride → phenyl-piperidin-4-yl-amine (23056-29-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) molecular sieves; 2) NaBH4 / 1) benzene, reflux, 20 h; 2) EtOH, room temp., 5 h 2: 92 percent / 6 N aq. HCl / H2O / 16 h / Heating View Scheme

N-ethoxycarbonyl-4-piperidone (29976-53-2) → phenyl-piperidin-4-yl-amine (23056-29-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) molecular sieves; 2) NaBH4 / 1) benzene, reflux, 20 h; 2) EtOH, room temp., 5 h 2: 92 percent / 6 N aq. HCl / H2O / 16 h / Heating View Scheme

4-piperidone hydrochloride (41979-39-9) + aniline (62-53-3) → phenyl-piperidin-4-yl-amine (23056-29-3)

Conditions	Yield
Stage #1: 4-piperidone hydrochloride; aniline With acetic acid; zinc at 20 - 70℃; for 24h; Stage #2: With sodium hydroxide In water Product distribution / selectivity; Cooling with ice;

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → phenyl-piperidin-4-yl-amine (23056-29-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 20 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium cyanoborohydride; acetic acid / methanol / 24 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C View Scheme

aniline (62-53-3) → phenyl-piperidin-4-yl-amine (23056-29-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 20 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C View Scheme

4-piperidone hydrochloride (41979-39-9) → phenyl-piperidin-4-yl-amine (23056-29-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 24 h / 20 °C 2: sodium cyanoborohydride; acetic acid / methanol / 24 h / 20 °C 3: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C View Scheme

styrene oxide (96-09-3) + phenyl-piperidin-4-yl-amine (23056-29-3) → 1-phenyl-2-(4-phenylamino-piperidin-1-yl)-ethanol (1269606-71-4)

Conditions	Yield
	85%

1-(3-chloropropoxy)-4-fluorobenzene (1716-42-3) + phenyl-piperidin-4-yl-amine (23056-29-3) → {1-[3-(4-Fluoro-phenoxy)-propyl]-piperidin-4-yl}-phenyl-amine

Conditions	Yield
With potassium carbonate; sodium iodide In 1,4-dioxane for 16h; Heating;	60%

1-isoquinolinecarbonitrile (1198-30-7) + phenyl-piperidin-4-yl-amine (23056-29-3) → N-phenyl-N-(piperidin-4-yl)isoquinoline-1-amine

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; 1,3-dicyano-5-fluoro-2,4,6-tris(diphenylamino)benzene In acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;	60%

C14H17Cl3N2O + phenyl-piperidin-4-yl-amine (23056-29-3) → C25H32Cl2N4O + C39H48Cl4N6O2

Conditions	Yield
With potassium carbonate In acetonitrile at 25℃; for 18h;	A 55% B n/a

4-chloro-1-(4-phenylpiperazin-1-yl)butan-1-one + phenyl-piperidin-4-yl-amine (23056-29-3) → C25H34N4O + C39H52N6O2

Conditions	Yield
With potassium carbonate In acetonitrile at 25℃; for 18h;	A 49% B n/a

C15H21ClN2O2 + phenyl-piperidin-4-yl-amine (23056-29-3) → C26H36N4O2 + C41H56N6O4

Conditions	Yield
With potassium carbonate In acetonitrile at 25℃; for 18h;	A 45% B n/a

1-(6-morpholinopyrimidin-4-yl)piperidine-4-carboxylic acid + phenyl-piperidin-4-yl-amine (23056-29-3) → (1-(6-morpholinopyrimidin-4-yl)piperidin-4-yl)(4-(phenylamino)piperidin-1-yl)methanone

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	41%

phenyl-piperidin-4-yl-amine (23056-29-3) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 1-(4-Fluoro-phenyl)-4-(4-phenylamino-piperidin-1-yl)-butan-1-one

Conditions	Yield
With potassium carbonate; sodium iodide In 1,4-dioxane for 16h; Heating;	35%

phenyl-piperidin-4-yl-amine (23056-29-3) + 5-({[1-(4-Chloro-phenyl)-methanoyl]-amino}-methyl)-thiophene-2-sulfonyl chloride (166964-34-7) → N-({5-[(4-anilinopiperidin-1-yl)sulfonyl]thien-2-yl}methyl)-4-chlorobenzamide

Conditions

Yield

Stage #1: phenyl-piperidin-4-yl-amine With polymer-bound morpholine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 5-({[1-(4-Chloro-phenyl)-methanoyl]-amino}-methyl)-thiophene-2-sulfonyl chloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 15h; Stage #3: With polymer-bound aminobenzene; polymer-bound isocyanate In dichloromethane; N,N-dimethyl-formamide at 20℃; for 5h;

4-chlorosulfonylbenzoyl chloride (7516-60-1) + phenyl-piperidin-4-yl-amine (23056-29-3) + 4-Br-2-[C(O)O-Wang resin]-aniline → 5-bromo-2-[4-(4-phenylamino-piperidine-1-sulfonyl)-benzoylamino]-benzoic acid

Conditions	Yield
Stage #1: 4-chlorosulfonylbenzoyl chloride; 4-Br-2-[C(O)O-Wang resin]-aniline With pyridine In dichloromethane at 20℃; for 4h; Stage #2: phenyl-piperidin-4-yl-amine With triethylamine In dichloromethane at 20℃; for 15h; Stage #3: With trifluoroacetic acid In dichloromethane at 20℃; for 1h;

6-hydroxy-1H-indole-2-carboxylic acid (40047-23-2) + phenyl-piperidin-4-yl-amine (23056-29-3) → C20H21N3O2

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide for 16h;

phenyl-piperidin-4-yl-amine (23056-29-3) → {1-[3-(4-Fluoro-phenoxy)-propyl]-piperidin-4-yl}-methyl-phenyl-amine

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / K2CO3, NaI / dioxane / 16 h / Heating 2: H2 / 10percent Pd/C / aq. ethanol / 16 h View Scheme

C21H18Cl3F6NO2 + phenyl-piperidin-4-yl-amine (23056-29-3) → C32H33Cl2F6N3O2

Conditions	Yield
With 3 A molecular sieve; sodium cyanoborohydride In CF3CH2OH at 23℃; for 4h;

C20H24N2O2 (1094173-12-2) + phenyl-piperidin-4-yl-amine (23056-29-3) → C31H38N4O (1094173-07-5)

Conditions	Yield
With polymer-supported carbodiimide; benzotriazol-1-ol In N,N-dimethyl-formamide at 50℃;

phenyl-piperidin-4-yl-amine (23056-29-3) + 1-phenyl-2-bromoethane (103-63-9) → (1-Phenethyl-piperidin-4-yl)-phenyl-amine (21409-26-7)

Conditions	Yield
With sodium hydroxide at 120℃; Product distribution / selectivity;

phenyl-piperidin-4-yl-amine (23056-29-3) + cyclopentanone (120-92-3) → (1-cyclopentyl-piperidin-4-yl)-phenyl-amine

Conditions	Yield
With sodium tris(acetoxy)borohydride In dichloromethane

C14H16N2O3S (34330-08-0) + phenyl-piperidin-4-yl-amine (23056-29-3) → C25H30N4O2S (1135023-95-8)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;

phenyl-piperidin-4-yl-amine (23056-29-3) + phenyl isothiocyanate (103-72-0) → C18H21N3S (1620774-22-2)

Conditions	Yield
In toluene at 20℃; for 2h;

phenyl-piperidin-4-yl-amine (23056-29-3) → 1-(2-(methylamino)ethyl)-N-phenylpiperidin-4-amine hydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 16 h / 20 °C 2: hydrogenchloride / dichloromethane; 1,4-dioxane / 2 h / 20 °C View Scheme

phenyl-piperidin-4-yl-amine (23056-29-3) + O-tert-butyl N-methyl-N-(2-oxoethyl)carbamate (123387-72-4) → C19H31N3O2

Conditions	Yield
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 16h;

Upstream product

• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 62-53-3 aniline 
• 41979-39-9 4-piperidone hydrochloride 
• 125541-22-2 1-(tert-butoxycarbonyl)-4-phenylaminopiperidine 
• 13035-19-3 4-aminopiperidine 
• 108-90-7 chlorobenzene 
• 108-86-1 bromobenzene 
• 29976-53-2 N-ethoxycarbonyl-4-piperidone 
• 116512-92-6 N-(1-ethoxycarbonyl-4-piperidinyl)aniline 

Downstream Products

• 1094173-07-5 C₃₁H₃₈N₄O 
• 21409-26-7 (1-Phenethyl-piperidin-4-yl)-phenyl-amine 
• 1269606-71-4 1-phenyl-2-(4-phenylamino-piperidin-1-yl)-ethanol 
• 1620774-22-2 C₁₈H₂₁N₃S 

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