Delmopinol Synthesis via Grignard Reaction
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Solution Overview
Problem
Current methods for producing delmopinol, a compound used in oral health, face challenges with low yield, high cost, and the use of restricted or non-commercially available materials, making them inefficient and costly for industrial-scale production.
Innovation Solution
A new process involving the use of 1-halo-4-propylhept-3-ene as a starting material, which allows for a more straightforward synthesis of delmopinol through a Grignard reaction with oxazolidin[2,3-c]morpholine, followed by catalytic hydrogenation, offering higher yields and improved purity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If current methods for producing delmopinol are used, then delmopinol can be synthesized, but the yield is low and the cost is high
Solution Approach 1:
The patent changes the chemical parameters by using 1-halo-4-propylhept-3-ene as a starting material instead of the conventional 4-propylheptan-1-ol. This parameter change in the molecular structure leads to improved reaction efficiency, higher yield, and reduced manufacturing cost through the Grignard reaction pathway described in the patent
Solution Approach 2:
The patent segments the synthesis pathway by introducing an intermediate compound (1-halo-4-propylhept-3-ene) that can be prepared separately and then used in the Grignard reaction. This segmentation allows for optimization of each step independently, improving overall productivity and reducing costs
2Productivity
If current methods for producing delmopinol are used, then delmopinol can be synthesized, but the number of steps is high and the process is complex
Solution Approach 1:
The patent extracts the double bond from the final product structure and incorporates it into the starting material (1-halo-4-propylhept-3-ene). This extraction allows the Grignard reaction to proceed directly to the desired product without requiring additional reduction steps, thereby reducing the total number of synthesis steps and simplifying the process
Solution Approach 2:
Instead of synthesizing the saturated alcohol first and then introducing functional groups, the patent inverts the approach by starting with the unsaturated halide and using it directly in the Grignard reaction. This inversion of the conventional synthesis route reduces process complexity and number of steps
3Ease of manufacture
If current methods for producing delmopinol are used, then delmopinol can be synthesized, but restricted or non-commercially available materials are required
Solution Approach 1:
The patent employs 1-halo-4-propylhept-3-ene as a starting material that can be prepared from commercially available compounds through a simple halogenation reaction. This replaces the need for restricted materials like -butyrolactone, using instead cheap, readily available reagents that can be disposed of or regenerated easily
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
This process reduces the number of steps, increases yield, and simplifies the production of delmopinol, making it more cost-effective and suitable for industrial-scale manufacturing while achieving high purity.
Implementation Method 1
The invention provides a process for the manufacturing of delmopinol, which process comprises the use of 1-halo-4-propylhept-3-ene. The invention further provides a process for manufacturing of delmopinol, which process comprises the use of 2-(3-(4-propylhept-3-en-1-yl)morpholino)ethan-1-ol.
Implementation Method 2
A new process involving the use of 1-halo-4-propylhept-3-ene as a starting material, which allows for a more straightforward synthesis of delmopinol through a Grignard reaction with oxazolidin[2,3-c]morpholine, followed by catalytic hydrogenation
Data Source
AI summary
The present invention relates to a new process for producing 2-(3-(4-propylheptyl)morpholino)ethan-1-ol with the INN name Delmopinol. The invention also relates to three key intermediates 1-chloro-4- propylhept-3-ene, 1-iodo-4-propylhept-3-ene and 2-(3-(4-propylhept-3-en-1-yl)morpholino)ethan-1-ol.