4-Pyrrolidinopyridine

Base Information

• Chemical Name: 4-Pyrrolidinopyridine
• CAS No.: 2456-81-7
• Molecular Formula: C9H12N2
• Molecular Weight: 148.208
• Hs Code.: 29333999
• European Community (EC) Number: 219-534-2
• UNII: DH59VKG9S4
• DSSTox Substance ID: DTXSID90179299
• Nikkaji Number: J174K
• Wikipedia: 4-Pyrrolidinylpyridine
• Wikidata: Q229878
• ChEMBL ID: CHEMBL4754833
• Mol file: 2456-81-7.mol

Synonyms:4-pyrrolidino-pyridine;4-pyrrolidinopyridine

Chemical Property of 4-Pyrrolidinopyridine

Chemical Property:

• Appearance/Colour: white crystal
• Vapor Pressure: 0.0105mmHg at 25°C
• Melting Point: 57-58 °C
• Refractive Index: 1.5378 (estimate)
• Boiling Point: 263.1 °C at 760 mmHg
• PKA: 9.58±0.10(Predicted)
• Flash Point: 142 °C
• PSA: 16.13000
• Density: 1.08 g/cm³
• LogP: 1.74680
• Storage Temp.: Store at RT.
• Solubility.: methanol: 0.1 g/mL, clear
• Water Solubility.: 3 g/L (21 ºC)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 148.100048391
• Heavy Atom Count: 11
• Complexity: 113

Purity/Quality:

98% ^*data from raw suppliers

4-Pyrrolidinopyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-34-41-23/24/25
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCN(C1)C2=CC=NC=C2
• General Description: 4-Pyrrolidinopyridine derivatives, particularly those derived from (S)-proline, serve as effective chiral catalysts for the enantioselective acylation of sec-alcohols. These catalysts utilize van der Waals and hydrogen-bonding interactions to achieve high selectivity in kinetic resolutions, with the hydroxyl group of the (S)-prolinol moiety playing a critical role in stereochemical control. Their modular synthesis and ability to facilitate remote stereocontrol make them promising tools for enantioselective acyl-transfer reactions.

Technology Process of 4-Pyrrolidinopyridine

There total 25 articles about 4-Pyrrolidinopyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

pyrrolidine (123-75-1) + 4-chlorpyridine hydrochloride (7379-35-3) → 4-pyrrolidin-1-ylpyridine (2456-81-7)

Guidance literature:

With sodium hydroxide; water; In 1,4-dioxane; at 70 ℃; for 20h; under 6000480 Torr;

Reference yield: 89.0%

pyrrolidine (123-75-1) + 4-Chloropyridine (626-61-9) → 4-pyrrolidin-1-ylpyridine (2456-81-7)

Guidance literature:

With zinc(II) nitrate hexahydrate; In acetonitrile; at 75 ℃; for 24h; Sealed tube; Green chemistry;

DOI:10.1002/cssc.201403154

Reference yield: 58.0%

N-Pyridin-4-yl-succinamic acid methyl ester; hydrochloride (121409-81-2) → 4-pyrrolidin-1-ylpyridine (2456-81-7)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; for 9h; Heating;

DOI:10.1055/s-1988-27777

upstream raw materials:

pyrrolidine

3-Bromopyridine

4-((trimethylsilyl)oxy)pyridine

N-trimethylsilylpyrrolidine

Downstream raw materials:

(2,6-diisopropylphenoxide)2(4-pyrrolidinopyridine)2-oxo-titanium(IV)

2,6-diisopropylbenzenamine

Ti(O)(2,6-diisopropylphenoxide)2(4-pyrrolidinopyridine)2

Refernces

Kinetic resolution of sec-alcohols using a new class of readily assembled (S)-proline-derived 4-(pyrrolidino)-pyridine analogues

10.1039/b419335k

The research details the development of a new class of chiral 4-(pyrrolidino)-pyridine catalysts derived from (S)-proline for the kinetic resolution of sec-alcohols. These catalysts, including compounds 4 and 5, leverage both van der Waals (π) and H-bonding interactions to achieve enantioselective acylation. The study involved synthesizing these catalysts from simple starting materials like 3-carboxy-4-chloropyridine and various amines. The catalysts were evaluated in the kinetic resolution of mono-protected diols in the presence of isobutyric anhydride, with the (S)-prolinol-derived catalysts showing significant enantioselectivity. The hydroxyl group in these catalysts was found to play a crucial role in determining the selectivity of the acylation reactions. The researchers also explored the influence of different substituents and the impact of H-bonding on the selectivity, using NMR spectroscopy to investigate possible aryl-pyridinium ion π-stacking interactions. The findings suggest that these catalysts represent a novel approach to achieving remote stereochemical control in acylation reactions, with potential applications in enantioselective acyl-transfer processes.