Delmopinol Salt Synthesis with Oxidation and Hydrogenation Steps
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
Existing methods for producing delmopinol and its salts are complex and inefficient, requiring multiple steps and potentially hazardous materials.
Innovation Solution
A method involving a series of controlled reactions using morpholine, hydrogen peroxide, sodium tungstate, p-toluenesulfonic acid, and metal salts to synthesize delmopinol and its salts, with specific solvent and pressure conditions, and optional use of protecting groups to simplify the process.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If existing commercial methods are used to produce delmopinol, then the production process is established and reliable, but the process complexity increases and efficiency decreases due to multiple synthetic steps
Solution Approach 1:
The synthesis process is divided into distinct sequential steps: oxidation of 4-heptanone to form the enone, hydrogenation to form the alcohol, and alkylation to form the final delmopinol product. Each step uses specific reagents and conditions optimized for that transformation, allowing the complex overall synthesis to be managed through modular, manageable stages while maintaining high overall efficiency
Solution Approach 2:
The patent employs parameter changes by using different solvents, temperatures, pressures, and catalysts for each synthetic step. For example, the oxidation uses H2O2 with Na2WO4·2H2O in a first solvent system, while hydrogenation uses H2 gas at high pressure (at least 10 kg/cm2) with Pd/C catalyst in a second solvent system. These parameter optimizations ensure each step proceeds efficiently with high yields
2Loss of time
If existing commercial methods are used to produce delmopinol, then the process is established, but hazardous materials and longer synthesis time are required
Solution Approach 1:
The patent employs readily available, inexpensive reagents such as hydrogen peroxide (H2O2) as the oxidant and catalytic amounts of sodium tungstate (Na2WO4·2H2O) and palladium on carbon (Pd/C) as catalysts. These reagents are consumed in the reaction and can be replaced, avoiding the need for expensive, hazardous, or hard-to-handle materials while maintaining high reaction efficiency and reducing synthesis time
Solution Approach 2:
The patent uses hydrogen peroxide (H2O2) as a strong, environmentally benign oxidant in place of traditional hazardous oxidizing agents. The oxidation of 4-heptanone to the enone intermediate proceeds efficiently with H2O2 in the presence of Na2WO4·2H2O catalyst, completing in reasonable time without requiring dangerous materials, thus reducing both synthesis time and hazardous material exposure
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
The method reduces the complexity and improves the efficiency of delmopinol and delmopinol salt production, ensuring high yields and purity through optimized reaction conditions and purification steps.
Implementation Method 1
contacting 4-heptanone with a first reaction mixture comprising: morpholine, a first solvent, H2O2, and Na2WO4·2H2O, where 4-hydroxy-4-propyl-1-heptene is formed
Implementation Method 2
contacting the 4-hydroxy-4-propyl-1-heptene with a second reaction mixture comprising: p-toluenesulfonic acid, a second solvent, H2 gas at a pressure of at least 10 kg/cm2, and Pd/C, where 4-hydroxy-4-propylheptane is formed
Implementation Method 3
contacting the 4-hydroxy-4-propylheptane with a third reaction mixture comprising: a third solvent, a salt (e.g., KI, NI, tetrabutylammonium iodide (TBAI), tetrabutylammonium bromide (TBAB), and the like), a base (which is optional), and a halogenated ethyl alcohol (e.g., 2-chloroethanol, 2-bromoethanol), ethylene oxide, or a halogenated ethane
Data Source
AI summary
Disclosed are methods of making delmopinol and delmopinol salts (e.g., delmopinol metal salts, such as, for example, delmopinol calcium salts, delmopinol sodium salts, delmopinol potassium salts, and/or delmopinol magnesium salts). Delmopinol has the following structure:and a salt of delmopinol has the following structure: