7663-77-6

Basic information

• Product Name: 1-(3-AMINOPROPYL)-2-PYRROLIDINONE
• Synonyms: 1-(3-AMINOPROPYL)-2-PYRROLIDONE;RARECHEM AL BW 2176;N-(3'-AMINOPROPYL)-2-PYRROLIDINONE;N-(3'-AMINOPROPYL)-2-PYRROLIDONE;1-(3-aminopropyl)-2-pyrrolidinon;2-Pyrrolidinone, 1-(3-aminopropyl)-;N-(3-aminopropyl)pyrrolidin-2-one;1-(3-Aminopropyl)pyrolidin-2-one
• CAS NO: 7663-77-6
• Molecular Formula: C₇H₁₄N₂O
• Molecular Weight: 142.2
• EINECS: 231-632-7
• Product Categories: Miscellaneous Reagents;Synthetic Intermediates;Building Blocks;Heterocyclic Building Blocks;Pyrrolidines;Amines;Heterocycles;Intermediates;Building Blocks;C4 to C8;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 7663-77-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 120-123 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to slightly brown/Liquid
• Density: 1.014 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.5(lit.)
• Storage Temp.: Refrigerator
• PKA: 9.85±0.10(Predicted)
• CAS DataBase Reference: 1-(3-AMINOPROPYL)-2-PYRROLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-AMINOPROPYL)-2-PYRROLIDINONE(7663-77-6)
• EPA Substance Registry System: 1-(3-AMINOPROPYL)-2-PYRROLIDINONE(7663-77-6)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3267 8/PG 2
• WGK Germany: 3
• RTECS: UY5739500
• F: 9-34
• Hazardous Substances Data: 7663-77-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 7663-77-6 differently. You can refer to the following data:
1. 1-(3-AMinopropyl)-2-pyrrolidinone can be used as a useful synthetic intermediate.
2. N-(3-Aminopropyl)-2-pyrrolidinone was used in the simultaneous determination of total polyamines and three of their non?α? amino acid metabolites in urine by capillary gas-chromatographic method with nitrogen-phosphorus detection.

General Description

N-(3-Aminopropyl)-2-pyrrolidinone (PYR) conjugates (VPA-PYR) of valproic acid (VA) have been investigated for their anticonvulsant activity in mice. It is the γ-lactam form of isoputreanine.

Synthetic route

DBN (3001-72-7) → 1-(3-aminopropyl)-2-pyrrolidone (7663-77-6)

Conditions	Yield
With water at 85℃; for 12h;	98%
With water at 85℃; for 12h;
With water at 20℃; for 12h;
With water In water-d2 at 27℃; Kinetics;

carbon monoxide (201230-82-2) + N-allyl-1,3-diaminopropane (34155-45-8) → 1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + octahydropyrrolo[1,2-a]pyrimidine (57672-23-8)

Conditions	Yield
With hydrogen; dirhodium tetraacetate In benzene at 80℃; under 20685.9 Torr; for 20h; Product distribution; PPh3 and other ligands;	A 90% B 10%
With dirhodium tetraacetate; hydrogen; triphenylphosphine In benzene at 80℃; under 20685.9 Torr; for 20h;
With dirhodium tetraacetate; hydrogen; tris-(o-tolyl)phosphine In benzene at 80℃; under 20685.9 Torr; for 20h; Product distribution; influence of gas composition, type of ligand;
With dirhodium tetraacetate; tributylphosphine; hydrogen In benzene at 80℃; under 20685.9 Torr; for 20h;

acrylonitrile (107-13-1) + 4-amino-n-butyric acid (56-12-2) → 1-(3-aminopropyl)-2-pyrrolidone (7663-77-6)

Conditions	Yield
With water at 120℃; Hydrieren des Reaktionsgemisches an Raney-Kobalt bei 120grad/200at.;

2-pyrrolidinon (616-45-5) + 3-bromopropylamine hydrochloride (5003-71-4) → 1-(3-aminopropyl)-2-pyrrolidone (7663-77-6)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide

3-[(prop-2-en-1-yl)amino]propanenitrile (34508-81-1) → 1-(3-aminopropyl)-2-pyrrolidone (7663-77-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / LiAlH4 2: H2, P(n-Bu)3, rhodium(II) acetate dimer / benzene / 20 h / 80 °C / 20685.9 Torr View Scheme

2-[3-(2-Oxo-pyrrolidin-1-yl)-propyl]-isoindole-1,3-dione (84598-48-1) → 1-(3-aminopropyl)-2-pyrrolidone (7663-77-6)

Conditions	Yield
With hydrazine hydrate

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + 2-([(tert-butoxy)carbonyl]{2-[(4-methoxybenzyl)amino]-2-oxoethyl}amino)acetic acid (194996-03-7) → [(4-Methoxy-benzylcarbamoyl)-methyl]-{[3-(2-oxo-pyrrolidin-1-yl)-propylcarbamoyl]-methyl}-carbamic acid tert-butyl ester (194996-16-2)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 16h; Substitution;	100%
With N,N-diethyl-N-isopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 16h;	27%

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + N-((tert-butyloxy)carbonyl)-N'-(2-(4-fluorophenyl)ethyl)iminodiacetic acid monoamide (188625-17-4) → N-((tert-butoxy)carbonyl)-N'-(2-(4-fluorophenyl)ethyl)-N''-(3-(N-pyrrolidin-2-onyl)propyl)iminodiacetic acid diamide (194996-17-3)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 16h; Substitution;	100%
With N,N-diethyl-N-isopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 16h;	18%

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + N-((tert-butyloxy)carbonyl)-N'-(2-(4-hydroxyphenyl)ethyl)iminodiacetic acid monoamide (194996-01-5) → {[2-(4-Hydroxy-phenyl)-ethylcarbamoyl]-methyl}-{[3-(2-oxo-pyrrolidin-1-yl)-propylcarbamoyl]-methyl}-carbamic acid tert-butyl ester (194996-14-0)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 16h; Substitution;	100%
With N,N-diethyl-N-isopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 16h;	9%

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + N-((tert-butyloxy)carbonyl)-N'-(4-(1',4'-dioxolano)piperidino)iminodiacetic acid monoamide (215161-22-1) → [2-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-2-oxo-ethyl]-{[3-(2-oxo-pyrrolidin-1-yl)-propylcarbamoyl]-methyl}-carbamic acid tert-butyl ester

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 16h; Substitution;	100%

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + 4-phenyl-1-butylamine (13214-66-9) + 3-bromomethylbenzoic acid (6515-58-8) → C33H39N3O4

Conditions	Yield
Multistep reaction.;	100%

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + C7H6BrClN2O (1393598-49-6) → C14H18N4O2 (1393598-31-6)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 85 - 95℃; Inert atmosphere;	100%

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + 3-(6-(benzyloxy)-9H-purin-9-yl)propanal → 1-(3-(3-(6-(benzyloxy)-9H-purin-9-yl)propylamino)propyl)pyrrolidin-2-one

Conditions	Yield
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 4h; Inert atmosphere;	100%

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + 4-fluoro-3-nitrobenzoyl chloride (400-94-2) → 4-fluoro-3-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-benzamide

Conditions	Yield
With triethylamine In dichloromethane at 23℃; for 1h;	98%

carbon disulfide (75-15-0) + 1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) → N-(3-isothiocyanatopropyl)-γ-butyrolactam (53485-01-1)

Conditions	Yield
With N-cyclohexylcarbodiimide In tetrahydrofuran at 20℃; for 5h;	98%

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + isocyanatodiphenylphosphine oxide (6779-62-0) → N-diphenylphosphoryl-N'-[3-(2-oxopyrrolidino)propyl]urea

Conditions	Yield
In acetonitrile at 20℃; for 1h; Inert atmosphere;	97.2%

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + ethyl 2-(1-ethoxyethylidene)hydrazinecarboxylate (51814-82-5, 51814-83-6, 58910-28-4) → 5-methyl-4-[3-(2-oxopyrrolidin-1-yl)propyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Conditions	Yield
In neat (no solvent) at 160 - 180℃; for 2h;	95.6%

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + (1R,2R)-2-[4-(2-Bromo-phenylsulfanyl)-2,3-dichloro-phenyl]-cyclopropanecarboxylic acid → (1S,2S)-2-[4-(2-Bromo-phenylsulfanyl)-2,3-dichloro-phenyl]-cyclopropanecarboxylic acid [3-(2-oxo-pyrrolidin-1-yl)-propyl]-amide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;	95%

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + 2-formyldimedone (16690-03-2) → 5,5-dimethyl-2-[3-(2-oxopyrrolidin-1-yl)propylaminomethylene]-1,3-cyclohexanedione

Conditions	Yield
In ethanol for 2h; Heating;	95%

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) → (E)-3-(4-hydroxy-3-methoxyphenyl)-N-(3-(2-oxopyrrolidin-1-yl)propyl)acrylamide

Conditions	Yield
at 85℃; for 0.05h; Microwave irradiation;	95%

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + iminodiacetic acid (142-73-4) → 1-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-piperazine-2,6-dione (1421691-43-1)

Conditions	Yield
at 85℃; for 0.05h; Microwave irradiation;	94%

3-[4-(N-methyl-N-phenylamino)pyrazolo[1,5-a]-1,3,5-triazin-8-yl]propionic acid (652538-76-6) + 1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) → N-[3-(2-oxopyrrolidin-1-yl)propyl]-3-[4-(N-methyl-N-phenylamino)pyrazolo[1,5-a]-1,3,5-triazin-8-yl]propionamide (934524-82-0)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	93%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	93%

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + 4-((2-fluorobenzyl)oxy)-3-methoxybenzaldehyde (423156-68-7) → 1-{3-[4-(2-Fluoro-benzyloxy)-3-methoxy-benzylamino]-propyl}-pyrrolidin-2-one

Conditions	Yield
Stage #1: 1-(3-aminopropyl)-2-pyrrolidone; 4-((2-fluorobenzyl)oxy)-3-methoxybenzaldehyde With titanium(IV) isopropylate In tetrahydrofuran at 20℃; for 12h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; ethanol at 70℃; for 6h;	91.6%

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + N-((tert-butyloxy)carbonyl)-N'-(5-((benzyloxycarbonyl)amino)-5-(methoxycarbonyl)pentyl)iminodiacetic acid monoamide (206867-09-6) → 2-benzyloxycarbonylamino-6-[2-(tert-butoxycarbonyl-{[3-(2-oxo-pyrrolidin-1-yl)-propylcarbamoyl]-methyl}-amino)-acetylamino]-hexanoic acid methyl ester

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 16h; Substitution;	91%

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + valinol (16369-05-4) + C21H21ClN3O4Pol + C21H21ClN3O4Pol + C21H21ClN3O4Pol + C21H21ClN3O4Pol + C21H21ClN3O4Pol + C22H23ClN3O4Pol + C22H23ClN3O4Pol + C21H22ClN4O4Pol + C25H23ClN3O4Pol + C25H23ClN3O4Pol + C25H23ClN3O4Pol + C25H23ClN3O4Pol + C25H23ClN3O4Pol + C25H23ClN3O4Pol + C25H23ClN3O4Pol + C25H27ClN5O4Pol + C25H27ClN5O4Pol + 2-Fluoroaniline (348-54-9) + indan-5-amine (24425-40-9) + 4-methoxy-aniline (104-94-9) + 2,4,6-trimethylaniline (88-05-1) + 6-amino-3,4-benzodioxane (22013-33-8) + N-methylaniline (100-61-8) → 1-{3-[9-isopropyl-6-(4-methoxy-benzylamino)-9H-purin-2-ylamino]-propyl}-pyrrolidin-2-one + NG-35 + 2-(2-fluorophenylamino)-6-(4-methoxybenzylamino)-9-isopropylpurine + 9-isopropyl-N6-(4-methoxy-benzyl)-N8-(4-methoxy-phenyl)-9H-purine-6,8-diamine + 2-(2,4,6-tri-methylphenylamino)-6-(4-methoxybenzylamino)-9-isopropylpurine + 2-(1,4-benzodioxan-6-amino)-6-(4-methoxybenzylamino)-9-isopropylpurine + 2-(indan-5-amino)-6-(4-methoxybenzylamino)-9-isopropylpurine + 2-(N-methylphenylamino)-6-(4-methoxybenzylamino)-9-isopropylpurine + 2-(4-methoxyphenylamino)-6-(4-methoxybenzylamino)-9-isopropylpurine + N-(4-methoxy-benzyl)-N'-(4-methoxy-phenyl)-pyrazine-2,3-diamine + N-(4-methoxy-benzyl)-N'-(4-methoxy-phenyl)-pyridazine-3,6-diamine + N-(4-methoxy-benzyl)-N'-(4-methoxy-phenyl)-pyrazine-2,6-diamine + N4-(4-methoxy-benzyl)-N2-(4-methoxy-phenyl)-pyrimidine-2,4-diamine + N-(4-methoxy-benzyl)-N'-(4-methoxy-phenyl)-pyrimidine-4,6-diamine + N4-(4-methoxy-benzyl)-N2-(4-methoxy-phenyl)-6-methyl-pyrimidine-2,4-diamine + N4-(4-methoxy-benzyl)-N2-(4-methoxy-phenyl)-5-methyl-pyrimidine-2,4-diamine + N'-(4-methoxy-benzyl)-N''-(4-methoxy-phenyl)-pyrimidine-2,4,6-triamine + N4-(4-methoxy-benzyl)-N6-(4-methoxy-phenyl)-quinazoline-4,6-diamine + N4-(4-methoxy-benzyl)-N2-(4-methoxy-phenyl)-quinazoline-2,4-diamine + N4-(4-methoxy-benzyl)-N7-(4-methoxy-phenyl)-quinazoline-4,7-diamine + N4-(4-methoxy-benzyl)-N8-(4-methoxy-phenyl)-quinazoline-4,8-diamine + N-(4-methoxy-benzyl)-N'-(4-methoxy-phenyl)-quinoxaline-2,3-diamine + N-(4-methoxy-benzyl)-N'-(4-methoxy-phenyl)-phthalazine-1,4-diamine + N4-(4-methoxy-benzyl)-N5-(4-methoxy-phenyl)-quinazoline-4,5-diamine

Conditions

Yield

Stage #1: 1-(3-aminopropyl)-2-pyrrolidone; valinol; C21H21ClN3O4Pol; C21H21ClN3O4Pol; C21H21ClN3O4Pol; C21H21ClN3O4Pol; C21H21ClN3O4Pol; C22H23ClN3O4Pol; C22H23ClN3O4Pol; C21H22ClN4O4Pol; C25H23ClN3O4Pol; C25H23ClN3O4Pol; C25H23ClN3O4Pol; C25H23ClN3O4Pol; C25H23ClN3O4Pol; C25H23ClN3O4Pol; C25H23ClN3O4Pol; C25H27ClN5O4Pol; C25H27ClN5O4Pol; 2-Fluoroaniline; indan-5-amine; 4-methoxy-aniline; 2,4,6-trimethylaniline; 6-amino-3,4-benzodioxane; N-methylaniline With potassium tert-butylate; tris-(dibenzylideneacetone)dipalladium(0); 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 1,4-dioxane at 80℃; for 12h; Polystyrene; Combinatorial reaction / High throughput screening (HTS); Stage #2: With dimethylsulfide; trifluoroacetic acid In dichloromethane; water for 2h;

A 90% B 83% C 80% D 85% E 81% F 91% G 88% H 91% I 90% J 86% K 87% L 89% M 90% N 90% O 90% P 91% Q 82% R 86% S 89% T 89% U 85% V 81% W 84% X 78%

...Expand

1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + methyl 6-amino-2,3-dichloropyrazine-5-carboxylate (1458-18-0) → methyl 3-amino-6-chloro-5-((3-(2-oxopyrrolidin-1-yl)propyl)amino)pyrazine-2-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	91%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Inert atmosphere;

Upstream product

• 84598-48-1 2-[3-(2-Oxo-pyrrolidin-1-yl)-propyl]-isoindole-1,3-dione 
• 34508-81-1 3-[(prop-2-en-1-yl)amino]propanenitrile 
• 616-45-5 2-pyrrolidinon 
• 5003-71-4 3-bromopropylamine hydrochloride 
• 201230-82-2 carbon monoxide 
• 34155-45-8 N-allyl-1,3-diaminopropane 
• 107-13-1 acrylonitrile 
• 56-12-2 4-amino-n-butyric acid 
• 3001-72-7 DBN 

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A comparative solid state 13C NMR and thermal study of CO 2 capture by amidines PMDBD and DBN

The present work shows study of the CO2 capture by amidines DBN and PMDBD using 13C solid-state NMR and thermal techniques. The solid state 13C NMR analyses demonstrate the formation of a single PMDBD-CO2 product which was assigned to stable bicarbonate. In the case of DBN, it is shown that two DBN-CO2 products are formed, which are suggested to be stable bicarbonate and unstable carbamate. The role of water in the DBN-CO2 capture as well as the stability of the products to environmental moisture was also investigated. The results suggest that the carbamate formation is favored in dry DBN, but in the presence of water it decompose to form bicarbonate. Thermal analysis shows a good gravimetric CO 2 absorption of DBN. Release of CO2 was found to be almost quantitative from the PMDBDH+ bicarbonate about 110 °C.