6-(Phthalimidomethyl)-6,11-dihydro-5H-dibenz[b,e]azepine
[CAS# 143878-20-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amide
• Name: 6-(Phthalimidomethyl)-6,11-dihydro-5H-dibenz[b,e]azepine
• Synonyms: 2-(6,11-dihydro-5H-benzo[c][1]benzazepin-6-ylmethyl)isoindole-1,3-dione
• Molecular Formula: C₂₃H₁₈N₂O₂
• Molecular Weight: 354.40
• CAS Registry Number: 143878-20-0
• EC Number: 629-841-7
• SMILES: C1C2=CC=CC=C2C(NC3=CC=CC=C31)CN4C(=O)C5=CC=CC=C5C4=O

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Boiling point: 557.3±29.0 °C 760 mmHg (Calc.)^*
• Flash point: 290.8±24.3 °C (Calc.)^*
• Index of refraction: 1.662 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H413
• Safety Statements: P264-P270-P273-P301+P312-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

6-(Phthalimidomethyl)-6,11-dihydro-5H-dibenz[b,e]azepine is a synthetic organic compound characterized by a dibenzazepine core structure substituted at the 6-position with a phthalimidomethyl group. Its molecular framework is based on the dibenzazepine scaffold, a bicyclic system comprising two benzene rings fused to a seven-membered azepine ring containing one nitrogen atom.

The dibenzazepine core is notable for its presence in several pharmacologically active compounds, particularly in the class of tricyclic antidepressants and anticonvulsants. The incorporation of the phthalimidomethyl substituent at the 6-position introduces additional functional versatility to the molecule. The phthalimide moiety is a bicyclic imide derived from phthalic anhydride and ammonia or primary amines, known for its stability and capacity to act as a masked amine protecting group or as a bioactive pharmacophore.

Synthetically, 6-(phthalimidomethyl)-6,11-dihydro-5H-dibenz[b,e]azepine can be prepared by functionalizing the dibenzazepine core at the 6-position through nucleophilic substitution or alkylation reactions using phthalimide derivatives or precursors such as phthalimidomethyl halides. The dibenzazepine framework itself is commonly constructed via intramolecular cyclization reactions or ring closure strategies starting from diarylamine or biphenyl derivatives.

The presence of the phthalimidomethyl group enhances the molecule's potential for further chemical transformations. The imide functionality is amenable to hydrolysis or hydrazinolysis, allowing conversion to primary amines after removal of the phthalimide protecting group. This characteristic makes the compound a useful intermediate in organic synthesis, particularly in the preparation of functionalized dibenzazepine derivatives with biological activity.

Pharmacologically, dibenzazepine derivatives have been extensively studied for their central nervous system effects, including antidepressant, antipsychotic, and anticonvulsant activities. While the specific biological activity of 6-(phthalimidomethyl)-6,11-dihydro-5H-dibenz[b,e]azepine may depend on further modifications or derivatives, its structural motifs align it with compounds known to interact with neurotransmitter systems, including serotonin and norepinephrine pathways.

The compound is typically characterized by standard analytical methods. Proton nuclear magnetic resonance (²H NMR) spectroscopy reveals signals corresponding to aromatic protons of the dibenzazepine core and the phthalimide group, as well as the methylene protons of the phthalimidomethyl substituent. Carbon-13 NMR (³C NMR) spectroscopy confirms the carbon environments, including carbonyl carbons of the imide and aromatic carbons. Infrared (IR) spectroscopy identifies characteristic imide carbonyl stretches near 1700 cm⁻¹. Mass spectrometry provides molecular weight confirmation and fragmentation patterns consistent with the molecular structure.

In terms of physical properties, 6-(phthalimidomethyl)-6,11-dihydro-5H-dibenz[b,e]azepine is expected to be a crystalline solid with moderate solubility in organic solvents such as dimethylformamide (DMF), dichloromethane, or chloroform. Its stability under standard laboratory conditions makes it suitable for use as a synthetic intermediate or for further functionalization in medicinal chemistry research.

In summary, 6-(phthalimidomethyl)-6,11-dihydro-5H-dibenz[b,e]azepine is a functionalized dibenzazepine derivative bearing a phthalimide substituent that confers synthetic versatility and potential biological relevance. It serves as an important intermediate in the synthesis of dibenzazepine-based compounds, which have broad applications in neuropharmacology and drug development.

References

2003. Epinastine hydrochloride. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-05-0032