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

General Description

4-Pyrrolidin-1-yl aniline is a chemical compound that consists of a pyrrolidine ring linked to an aniline group. It is a versatile building block in organic synthesis, commonly used in the production of pharmaceuticals, agrochemicals, and materials science. 4-PYRROLIDIN-1-YLANILINE is known for its ability to form stable complexes with metal ions, making it an important component in coordination chemistry. Additionally, 4-Pyrrolidin-1-yl aniline has been studied for its potential use in the development of new materials with specific electronic and optical properties. Its unique structure and reactivity make it a valuable tool in the field of chemical research and development.

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

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

Downstream Products

• 855624-33-8 N,N-bis-(3-cyano-propyl)-4-pyrrolidino-aniline 
• 109595-59-7 methyl-[1,4]benzoquinone-4-(4-pyrrolidino-phenylimine) 
• 854859-04-4 4,4'-(4-pyrrolidino-phenylimino)-di-butyric acid dimethyl ester 
• 1002158-46-4 N-(4-((4-(pyrrolidin-1-yl)phenylamino)methyl)benzyl)pyrimidin-2-amine 

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