3-(3-Methyl-2-oxo-4-(3-(piperidin-4-yloxy)prop-1-yn-1-yl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidine-2,6-dione
[CAS# 2434846-91-8]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Piperidines
• Name: 3-(3-Methyl-2-oxo-4-(3-(piperidin-4-yloxy)prop-1-yn-1-yl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidine-2,6-dione
• Molecular Formula: C₂₁H₂₄N₄O₄
• Molecular Weight: 396.44
• CAS Registry Number: 2434846-91-8
• SMILES: O=C(C(N(C1=CC=CC(C#CCOC2CCNCC2)=C1N3C)C3=O)CC4)NC4=O

Discovery and Applications

3-(3-Methyl-2-oxo-4-(3-(piperidin-4-yloxy)prop-1-yn-1-yl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidine-2,6-dione is a multifunctional heterocyclic compound commonly used as an intermediate in medicinal chemistry for the synthesis of biologically active molecules. The compound contains a piperidine-2,6-dione (glutarimide) core substituted at the 3-position with a 3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole unit, which is further substituted at the 4-position with a 3-(piperidin-4-yloxy)prop-1-yn-1-yl side chain. This architecture combines multiple heterocycles and functional groups, providing opportunities for selective derivatization and incorporation into complex drug-like scaffolds.

The prop-1-yn-1-yl linker offers a site for additional coupling reactions, such as Sonogashira cross-coupling or nucleophilic additions, while the piperidin-4-yloxy group provides a basic site that can participate in further functionalization. The benzimidazole and glutarimide units contribute to hydrogen bonding interactions and planarity, which are useful for binding to biological targets, particularly in programs exploring enzyme inhibitors, receptor modulators, or other heterocyclic small-molecule therapeutics. The methyl and oxo substituents on the benzimidazole further tune the electronic properties and steric environment of the molecule, facilitating structure-activity relationship optimization.

This compound is typically handled as a solid under standard laboratory conditions and may require protection from moisture or strong acids and bases to preserve its functional groups. Analytical verification using NMR spectroscopy, mass spectrometry, and HPLC is commonly employed to ensure purity and structural integrity prior to its use in multi-step synthetic sequences.