(1S,2S,5S)-4-[2-[2-(6,6-Dimethylbicyclo[3.1.1]hept-2-yl)ethoxy]ethyl]morpholine
[CAS# 38284-47-8]

Identification

• Classification: Organic raw materials >> Ether compounds and their derivatives
• Name: (1S,2S,5S)-4-[2-[2-(6,6-Dimethylbicyclo[3.1.1]hept-2-yl)ethoxy]ethyl]morpholine
• Synonyms: 4-[2-[2-(6,6-dimethyl-2-bicyclo[3.1.1]heptanyl)ethoxy]ethyl]morpholine
• Molecular Formula: C₁₇H₃₁NO₂
• Molecular Weight: 281.43
• CAS Registry Number: 38284-47-8
• EC Number: 609-541-2
• SMILES: CC1(C2CCC(C1C2)CCOCCN3CCOCC3)C

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.484, Calc.^*
• Boiling Point: 356.2±22.0 ºC (760 mmHg), Calc.^*
• Flash Point: 101.4±11.0 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P280-P305+P351+P338

Discovory and Applicatios

(1S,2S,5S)-4-[2-[2-(6,6-Dimethylbicyclo[3.1.1]hept-2-yl)ethoxy]ethyl]morpholine is an organic compound that features a morpholine ring substituted with a bulky bicyclic moiety. This compound contains a total of seventeen carbon atoms, thirty-one hydrogen atoms, one nitrogen atom, and two oxygen atoms, and its stereochemistry is defined at three chiral centers as (1S,2S,5S). The molecule combines both heterocyclic and bicyclic structures, which contributes to its stability and physicochemical behavior.

The compound is primarily recognized in pharmaceutical manufacturing as an identified process-related impurity in the synthesis of pinaverium bromide. Pinaverium bromide is a quaternary ammonium compound used as a gastrointestinal calcium channel blocker. During its multistep synthesis, several by-products or side products may form due to incomplete reactions or rearrangements. (1S,2S,5S)-4-[2-[2-(6,6-Dimethylbicyclo[3.1.1]hept-2-yl)ethoxy]ethyl]morpholine is one of these by-products, and it must be monitored carefully to ensure the purity of the final pharmaceutical product. Regulations require that such impurities are either removed or their concentrations kept below acceptable thresholds to ensure patient safety.

Beyond its identification as an impurity, the compound is also relevant in the development of analytical techniques used in pharmaceutical quality control. Because impurities can affect the pharmacological properties of medications, including safety and efficacy, they must be quantified accurately. This compound has been used as a reference standard in analytical method validation, particularly in chromatographic methods designed to detect and quantify impurities in finished drug products. High-performance liquid chromatography (HPLC) and gas chromatography (GC) are commonly employed techniques for this purpose, often paired with mass spectrometric detection.

From a chemical perspective, the molecule's morpholine ring is a common structural motif found in various pharmacologically active substances, known for contributing to solubility and metabolic stability. The bicyclo[3.1.1]heptane unit, often referred to as a camphane-like structure, adds to the rigidity and hydrophobic character of the compound. The presence of a terminal morpholine group connected via a flexible ethylene glycol-type linker to a rigid, sterically hindered bicyclic system makes this molecule structurally distinctive.

This compound is available from commercial chemical suppliers in small quantities for research and reference purposes. It is typically handled as a solid or low-viscosity liquid and stored under refrigerated conditions to preserve its chemical stability over time. Handling guidelines recommend minimizing exposure to moisture and light, as such conditions may induce degradation or structural changes.

Physicochemical properties of the compound include a reported density close to 0.99 g/cm³ and a boiling point in excess of 350 °C under standard atmospheric pressure. These properties reflect the molecular weight and relatively low volatility of the compound, which is consistent with its function as a stable reference standard in analytical applications.

In conclusion, (1S,2S,5S)-4-[2-[2-(6,6-Dimethylbicyclo[3.1.1]hept-2-yl)ethoxy]ethyl]morpholine is a well-characterized chemical substance of importance in the pharmaceutical industry. It plays a crucial role in impurity profiling and method validation during the production of pinaverium bromide. Its structural complexity and defined stereochemistry make it a suitable candidate for use as a reference standard in quality assurance processes, thereby contributing to the safe and effective manufacture of pharmaceutical compounds.