1-Methylazepan-4-one Hydrochloride | Key Intermediate for Pharmaceutical Synthesis
Product Concept
1-Methylazepan-4-one Hydrochloride (CAS To Be Confirmed) is a versatile seven-membered cyclic amine derivative, widely recognized as a privileged scaffold in modern medicinal chemistry. This chiral bicyclic compound features a ketone group at the 4-position and a methyl substitution at the 1-position, making it an essential building block for synthesizing neurologically active compounds. With its rigid azepane structure and protonated amine group, this hydrochloride salt demonstrates superior solubility in polar solvents compared to its free base form, particularly in methanol (>200 mg/mL) and aqueous solutions. Its unique structural properties enable precise molecular interactions in complex chemical environments.
Technical Specifications
- Molecular Formula: C₇H₁₄ClNO
- Molecular Weight: 171.65 g/mol
- Appearance: White to off-white crystalline powder
- Purity: ≥98% (HPLC)
- Optical Rotation: [α]²⁰D = +15° to +25° (c=1, H₂O)
- Storage: 2-8°C in a desiccator
Mechanistic Action
This compound serves as:
- Dopamine Receptor Modulator: The azepane scaffold mimics natural neurotransmitter structures, enabling targeted receptor interactions.
- Chiral Auxiliary: Facilitates enantioselective synthesis of β-amino alcohol derivatives.
- Hydrogen Bond Acceptor: Enhances molecular recognition in host-guest systems.
- Proton Sponge: Provides buffering capacity in catalytic reactions (pH 3.5-5.5).
Multidisciplinary Applications
Pharmaceutical Development
- Antidepressants: Core structure for SSRIs and SNRIs synthesis.
- Antipsychotics: Dopamine D3 receptor-targeted agents.
- Analgesics: μ-opioid receptor modulators.
- Antivirals: Precursor for HIV protease inhibitors.
Organic Synthesis
- Substrate for Buchwald-Hartwig amination.
- Template for asymmetric hydrogenation.
- Precursor for ring-closing metathesis reactions.
Material Science
- Component of ionic liquids for CO₂ capture.
- Modifier for self-assembled monolayers (SAMs).
- Additive for chiral stationary phases in chromatography.
Synthetic Pathway
- Starting Material: Cycloheptanone.
- Mannich Reaction: Introduction of methylamine group.
- Catalytic Hydrogenation: Pd/C-mediated selective reduction.
- Chiral Resolution: Enantiomer separation using L-tartaric acid.
- Hydrochloride Formation: Crystallization in HCl/Et₂O system.
Analytical Methods
- Purity: HPLC-ELSD (Phenomenex Luna 5μ C18 column).
- Structure: ¹H/¹³C NMR (600 MHz, D₂O).
- Chirality: Chiralpak AD-H column analysis.
- Residual Solvents: GC-MS per ICH Q3C guidelines.
Safety Protocols
- LD₅₀ (oral, rat): >2000 mg/kg.
- Skin Irritation: Complies with GHS Category 3.
- Waste Disposal: Degradation via alkaline hydrolysis.
- Transport Classification: UN2811, Class 6.1 hazardous material.