2632-65-7

Basic information

• Product Name: 4-PYRROLIDIN-1-YLANILINE
• Synonyms: ART-CHEM-BB B021942;4-PYRROLIDIN-1-YL-PHENYLAMINE;4-PYRROLIDIN-1-YLANILINE;4-(1-PYRROLIDINYL)ANILINE;AKOS B021942;AKOS BB-8560;TIMTEC-BB SBB009578;4-(1-pyrrolidinyl)phenylamine
• CAS NO: 2632-65-7
• Molecular Formula: C₁₀H₁₄N₂
• Molecular Weight: 162.23
• Mol File: 2632-65-7.mol
• Article Data: 26

Chemical Properties

• Melting Point: 51 °C
• Boiling Point: 330.8 °C at 760 mmHg
• Flash Point: 131.3 °C
• Appearance: /
• Density: 1.109 g/cm³
• Vapor Pressure: 0.000162mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 7.20±0.40(Predicted)
• CAS DataBase Reference: 4-PYRROLIDIN-1-YLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PYRROLIDIN-1-YLANILINE(2632-65-7)
• EPA Substance Registry System: 4-PYRROLIDIN-1-YLANILINE(2632-65-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 2632-65-7(Hazardous Substances Data)

Usage

Description

4-Pyrrolidin-1-yl aniline is a chemical compound characterized by a pyrrolidine ring connected to an aniline group. It serves as a versatile building block in organic synthesis, playing a crucial role in the creation of pharmaceuticals, agrochemicals, and materials science. Known for its capacity to form stable complexes with metal ions, 4-Pyrrolidin-1-yl aniline is a significant component in coordination chemistry. Furthermore, it has been investigated for its potential in developing new materials with tailored electronic and optical properties, making it a valuable asset in chemical research and development due to its distinctive structure and reactivity.

Uses

Used in Pharmaceutical Industry:
4-Pyrrolidin-1-yl aniline is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to form stable complexes with metal ions, which can enhance the efficacy and stability of drug molecules.
Used in Agrochemical Industry:
In agrochemicals, 4-Pyrrolidin-1-yl aniline is utilized as a building block for the development of new compounds that can improve crop protection and yield by targeting specific pests or diseases.
Used in Materials Science:
4-Pyrrolidin-1-yl aniline is employed as a component in the creation of advanced materials with unique electronic and optical properties, contributing to the advancement of technologies in areas such as electronics, photonics, and energy storage.
Used in Coordination Chemistry:
As a vital component in coordination chemistry, 4-Pyrrolidin-1-yl aniline is used to form complexes with metal ions, which can be applied in various fields including catalysis, sensing, and the development of new materials with specialized functions.
Used in Chemical Research and Development:
4-Pyrrolidin-1-yl aniline is utilized as a valuable tool in chemical research and development due to its unique structure and reactivity, enabling the exploration of new synthetic pathways and the discovery of novel compounds with potential applications across various industries.

InChI:InChI=1/C10H14N2/c11-9-3-5-10(6-4-9)12-7-1-2-8-12/h3-6H,1-2,7-8,11H2

Synthetic route

4-(1-oxy-pyrrolidin-1-yl)-phenylamine → 4-pyrrolidin-1-yl-aniline (2632-65-7)

Conditions	Yield
With copper(l) iodide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 35 - 40℃; for 3h;	96%

1-(4-nitro-phenyl)-pyrrolidine (10220-22-1) → 4-pyrrolidin-1-yl-aniline (2632-65-7)

Conditions	Yield
With hydrogen In methanol; ethyl acetate at 100℃; for 0.333333h; Flow reactor; Green chemistry; chemoselective reaction;	93%
With ammonium chloride; zinc In tetrahydrofuran; methanol at 0 - 20℃; for 18h;	91.2%
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 9h; Inert atmosphere; Schlenk technique;	85%

1-(4-nitrophenyl)piperidine (6574-15-8) → 4-pyrrolidin-1-yl-aniline (2632-65-7)

Conditions	Yield
With palladium 10% on activated carbon; hydrazine hydrate In ethanol for 12h; Reflux;	80%

1-(4-bromo-phenyl)-pyrrolidine (22090-26-2) → 4-pyrrolidin-1-yl-aniline (2632-65-7)

Conditions	Yield
Stage #1: 1-(4-bromo-phenyl)-pyrrolidine With magnesium In tetrahydrofuran Inert atmosphere; Stage #2: With C10H17NO In tetrahydrofuran; toluene at -78℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water; toluene Inert atmosphere;	57%

pyrrolidine (123-75-1) + 4-bromo-aniline (106-40-1) → 4-pyrrolidin-1-yl-aniline (2632-65-7)

Conditions	Yield
With cesium hydroxide In dimethyl sulfoxide at 120℃; for 0.166667h;	52%

1-(4-nitroso-phenyl)-pyrrolidine; hydrochloride → 4-pyrrolidin-1-yl-aniline (2632-65-7)

Conditions	Yield
With hydrogenchloride; tin

1,4-dichlorobutane (110-56-5) + 1,4-phenylenediamine (106-50-3) → 4-pyrrolidin-1-yl-aniline (2632-65-7)

Conditions	Yield
With 1,2-dichloro-benzene at 110℃;

tetrahydrofuran (109-99-9) + 1,4-phenylenediamine (106-50-3) → 4-pyrrolidin-1-yl-aniline (2632-65-7) + 1,4-di(pyrrolidin-1-yl)benzene (50771-64-7)

Conditions	Yield
titanium(IV) oxide at 250 - 300℃; Yield given. Yields of byproduct given;

4-chlorobenzonitrile (100-00-5) → 4-pyrrolidin-1-yl-aniline (2632-65-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol 2: nickel-chromium oxide catalyst; methanol / 80 °C / 147102 Torr / Hydrogenation View Scheme
Multi-step reaction with 2 steps 2: Raney nickel; ethanol / 60 °C / 2206.5 Torr / Hydrogenation View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate; Aliquat (at)366 / N,N-dimethyl-formamide / 24 h / 100 °C 2: ammonium hydroxide; sodium dithionite / water / 0.25 h / Reflux View Scheme

C15H22N2O2 (1258532-14-7) → 4-pyrrolidin-1-yl-aniline (2632-65-7)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 6h;

para-nitrophenyl bromide (586-78-7) → 4-pyrrolidin-1-yl-aniline (2632-65-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / Reflux 2: hydrogen; palladium 10% on activated carbon / methanol / 20 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate; tertamethylammonium iodide / dimethyl sulfoxide / 12 h / 80 °C 2: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 3 h / 20 °C View Scheme

4-Fluoronitrobenzene (350-46-9) → 4-pyrrolidin-1-yl-aniline (2632-65-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / dimethyl sulfoxide / 20 °C / Inert atmosphere; Schlenk technique 2: hydrogen; palladium 10% on activated carbon / ethanol / 9 h / 20 °C / Inert atmosphere; Schlenk technique View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 110 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrazine hydrate / ethanol / 12 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 40 °C 2: 5%-palladium/activated carbon; hydrogen / ethanol; water / 20 °C View Scheme

4-pyrrolidin-1-yl-aniline (2632-65-7) + 9-(cyclopentyl)-2,6-(dichloro)-9H-purine (211733-67-4) → (2-chloro-9-cyclopentyl-9H-purin-6-yl)-(4-pyrrolidin-1-yl-phenyl)amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In propan-1-ol at 100℃; Inert atmosphere; Sealed tube;	92%
With N-ethyl-N,N-diisopropylamine In propan-1-ol at 100℃; Sealed tube; Inert atmosphere;	92%

4-pyrrolidin-1-yl-aniline (2632-65-7) + Glyoxal (131543-46-9) → N,N'-(1,2-ethanediylidene)bis(4-pyrrolidin-1-ylbenzeneamine) (1172626-91-3)

Conditions	Yield
In propan-1-ol; water at 70℃; for 24h; Inert atmosphere;	91%

4-pyrrolidin-1-yl-aniline (2632-65-7) + C14H14ClN5O2 → 3-(3,5-dimethoxyphenethyl)-N-(4-(pyrrolidin-1-yl)phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine

Conditions	Yield
In butan-1-ol at 100℃; Inert atmosphere; Schlenk technique;	90%

4-pyrrolidin-1-yl-aniline (2632-65-7) + N-benzyloxycarbonyl isoleucine (3160-59-6, 4276-05-5, 28862-89-7, 55723-45-0, 55723-48-3, 127866-12-0) → Cbz-Ile-4-pyrrolidynylanilide

Conditions	Yield
Stage #1: N-benzyloxycarbonyl isoleucine With 1-methyl-1H-imidazole In dichloromethane at 0 - 5℃; for 0.166667h; Stage #2: With methanesulfonyl chloride In dichloromethane at -5℃; for 0.333333h; Stage #3: 4-pyrrolidin-1-yl-aniline In dichloromethane at 20℃; for 2h;	89%

succinic acid anhydride (108-30-5) + 4-pyrrolidin-1-yl-aniline (2632-65-7) → 4-(4-(pyrrolidin-1-yl)phenylamino)-4-oxobutanoic acid

Conditions	Yield
In dichloromethane at 20℃; for 24h; Cooling;	87%

4-pyrrolidin-1-yl-aniline (2632-65-7) + 25,26,27,28-tetraproxycalix[4]arene-5,17-dicarboxoyl chloride (191880-48-5) → 5,17-bis(N-(4-(pyrrolidin-1-yl)phenyl)aminocarbonyl)-25,26,27,28-tetrapropoxycalix<4>arene

Conditions	Yield
With triethylamine In dichloromethane at 25℃; for 1h;	85%

4-pyrrolidin-1-yl-aniline (2632-65-7) + 5-fluoro-2-hydroxybenzaldehyde (347-54-6) → 4-(1-pyrrolidinyl)-benzenamine salicylaldehyde

Conditions	Yield
In ethanol for 8h; Reflux;	83.7%

Z-Leu-OH (2018-66-8) + 4-pyrrolidin-1-yl-aniline (2632-65-7) → Cbz-Leu-4-pyrrolidynylanilide (1286716-55-9)

Conditions	Yield
Stage #1: Z-Leu-OH With 1-methyl-1H-imidazole In dichloromethane at 0 - 5℃; for 0.166667h; Stage #2: With methanesulfonyl chloride In dichloromethane at -5℃; for 0.333333h; Stage #3: 4-pyrrolidin-1-yl-aniline In dichloromethane at 20℃; for 2h;	83%

4-pyrrolidin-1-yl-aniline (2632-65-7) + 4-Fluoronitrobenzene (350-46-9) → N,N-bis(4-nitrophenyl)-4-(pyrrolidin-1-yl)aniline

Conditions	Yield
With cesium fluoride In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;	75%

2-tert-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (898270-94-5) + 4-pyrrolidin-1-yl-aniline (2632-65-7) → 2-tert-butyl-5-phenyl-4-[(4-pyrrolidin-1-ylphenyl)amino]isothiazol-3(2H)-one 1,1-dioxide

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide; acetonitrile at 120℃; for 1h; Microwave irradiation;	69%

4-pyrrolidin-1-yl-aniline (2632-65-7) + 7-chloro-5-cyclopentyl-[1,2,4]triazolo[4,3-f]pteridin-4(5H)-one → 5-cyclopentyl-7-((4-(pyrrolidin-1-yl)phenyl)amino)-[1,2,4]triazolo[4,3-f]pteridin-4(5H)-one

Conditions	Yield
With toluene-4-sulfonic acid In butan-1-ol at 100℃; for 15h;	66.1%

4-pyrrolidin-1-yl-aniline (2632-65-7) + 2,5-dichloro-4-(3-nitrophenoxy)pyrimidine (76661-24-0) → 5-chloro-4-(3-nitrophenoxy)-N-(4-(pyrrolidin-1-yl)phenyl)pyrimidin-2-amine

Conditions	Yield
With trifluoroacetic acid In iso-butanol at 100℃;	65.7%

4-pyrrolidin-1-yl-aniline (2632-65-7) + 7-chloro-5-cyclopentyl-tetrazolo[4,3-f]pteridin-4(5H)-one → 5-cyclopentyl-7-((4-(pyrrolidin-1-yl)phenyl)amino)tetrazolo[1,5-f]pteridin-4(5H)-one

Conditions	Yield
With toluene-4-sulfonic acid In butan-1-ol at 100℃; for 15h;	65.2%

4-pyrrolidin-1-yl-aniline (2632-65-7) → 2-iodo-4-(pyrrolidin-1-yl)aniline

Conditions	Yield
With hydrogenchloride; potassium iodate; potassium iodide In methanol; water	63%

4-pyrrolidin-1-yl-aniline (2632-65-7) + 7-chloro-5-cyclopentyl-1-methyl-[1,2,4]triazolo[4,3-f]pteridin-4(5H)-one → 5-cyclopentyl-1-methyl-7-((4-(pyrrolidin-1-yl)phenyl)amino)-[1,2,4]triazolo[4,3-f]pteridin-4(5H)-one

Conditions	Yield
With toluene-4-sulfonic acid In butan-1-ol at 100℃; for 15h;	55.7%

4-pyrrolidin-1-yl-aniline (2632-65-7) + 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide (302964-08-5) → N-(2-chloro-6-methylphenyl)-2-((2-methyl-6-((4-(pyrrolidin-1-yl)phenyl)amino)pyrimidin-4-yl)amino)thiazole-5-carboxamide (1587622-99-8)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 110℃; for 12h;	49%

4-pyrrolidin-1-yl-aniline (2632-65-7) + (4-((6,7-dimethoxyquinazolin-4-yl)oxy)-2,6-difluorophenyl)-2-oxoacetic acid → 2-(4-((6,7-dimethoxyquinazolin-4-yl)oxy)-2,6-difluorophenyl)-N-(4-(pyrrolidin-1-yl)phenyl)-2-oxoacetamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In acetonitrile at 20℃; for 12h;	47%

4-pyrrolidin-1-yl-aniline (2632-65-7) + C15H11Cl2FN6 → 4-(3-(3-chloro-4-fluorophenyl)-5,6-dihydro-[1,2,4]triazolo-[4,3-a]pyrazin-7(8H)-yl)-N-(4-(pyrrolidin-1-yl)phenyl)pyrimidin-2-amine

Conditions	Yield
With toluene-4-sulfonic acid In isopropyl alcohol at 90℃; for 24h;	30%

(S)-4-methyl-2-(toluene-4-sulfonamido)pentanoic acid (1220-80-0, 67368-40-5, 150614-61-2) + 4-pyrrolidin-1-yl-aniline (2632-65-7) → (S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(4-(pyrrolidin-1-yl)phenyl)pentanamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 18h; Inert atmosphere;	24%

indole (120-72-9) + 4-pyrrolidin-1-yl-aniline (2632-65-7) + oxalyl dichloride (79-37-8) → 2-(1H-indol-3-yl)-2-oxo-N-(4-(pyrrolidin-1-yl)phenyl)acetamide (1257651-78-7)

Conditions	Yield
Stage #1: indole; oxalyl dichloride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: 4-pyrrolidin-1-yl-aniline With 2,6-dimethylpyridine; dmap In tetrahydrofuran at 45℃; for 18h; Inert atmosphere;	16%

4-pyrrolidin-1-yl-aniline (2632-65-7) + 3-(2,6-dichlorophenyl)-7-methylsulfanyl-2H-pyrimido[5,4-e][1,3]oxazin-4-one → 3-(2,6-dichlorophenyl)-7-((4-(pyrrolidin-1-yl)phenyl)amino)-2,3-dihydro-4H-pyrimido[5,4-e][1,3]oxazin-4-one

Conditions	Yield
Stage #1: 3-(2,6-dichlorophenyl)-7-methylsulfanyl-2H-pyrimido[5,4-e][1,3]oxazin-4-one With 3-chloro-benzenecarboperoxoic acid In toluene at 20℃; for 0.5h; Stage #2: 4-pyrrolidin-1-yl-aniline With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 12h;	14.66%

4-pyrrolidin-1-yl-aniline (2632-65-7) + 3-fluoro-5-formyl-4-hydroxybenzoic acid → 1-(3-fluoro-5-formyl-4-hydroxyphenyl)-3-(4-(pyrrolidin-1-yl)phenyl)urea

Conditions	Yield
Stage #1: 4-pyrrolidin-1-yl-aniline; 3-fluoro-5-formyl-4-hydroxybenzoic acid In 1,4-dioxane at 20℃; for 0.166667h; Stage #2: With diphenyl phosphoryl azide; triethylamine In 1,4-dioxane at 20 - 90℃; for 3.5h; Stage #3: With hydrogenchloride In water at 20℃; for 1h;	7%

4-pyrrolidin-1-yl-aniline (2632-65-7) + 3-fluoro-5-formyl-4-hydroxybenzene-1-sulfonyl chloride → 3-fluoro-5-formyl-4-hydroxy-N-(4-(pyrrolidin-1-yl)phenyl)benzenesulfonamide

Conditions	Yield
Stage #1: 4-pyrrolidin-1-yl-aniline; 3-fluoro-5-formyl-4-hydroxybenzene-1-sulfonyl chloride With 4-methyl-morpholine In dichloromethane for 5h; Stage #2: With hydrogenchloride In dichloromethane for 3h;	4%

4-pyrrolidin-1-yl-aniline (2632-65-7) + 4-iodobutyronitrile (6727-73-7) → N,N-bis-(3-cyano-propyl)-4-pyrrolidino-aniline (855624-33-8)

Conditions	Yield
With water; potassium carbonate; sodium hydrogensulfite

Upstream product

• 22090-26-2 1-(4-bromo-phenyl)-pyrrolidine 
• 6574-15-8 1-(4-nitrophenyl)piperidine 
• 350-46-9 4-Fluoronitrobenzene 
• 586-78-7 para-nitrophenyl bromide 
• 1258532-14-7 C₁₅H₂₂N₂O₂ 
• 100-00-5 4-chlorobenzonitrile 
• 123-75-1 pyrrolidine 
• 106-40-1 4-bromo-aniline 
• 109-99-9 tetrahydrofuran 
• 106-50-3 1,4-phenylenediamine 
• 110-56-5 1,4-dichlorobutane 
• 10220-22-1 1-(4-nitro-phenyl)-pyrrolidine 

Downstream Products

• 1144072-79-6 1-{4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}-3-(4-pyrrolidin-1-ylphenyl)urea 
• 1002158-46-4 N-(4-((4-(pyrrolidin-1-yl)phenylamino)methyl)benzyl)pyrimidin-2-amine 
• 1172626-91-3 N,N'-(1,2-ethanediylidene)bis(4-pyrrolidin-1-ylbenzeneamine) 
• 348626-23-3 5-Chloro-N-({(5S)-2-oxo-3-[4-(1-pyrrolidinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophenecarboxamide 
• 854859-04-4 4,4'-(4-pyrrolidino-phenylimino)-di-butyric acid dimethyl ester 
• 949001-19-8 C₂₀H₂₅N₇O₂ 
• 916646-21-4 C₁₇H₁₇N₃O₄ 

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