Meglumine synthesis
- Product Name:Meglumine
- CAS Number:6284-40-8
- Molecular formula:C7H17NO5
- Molecular Weight:195.21
Yield:6284-40-8 62.5%
Reaction Conditions:
with hydrogen in water at 10 - 100; under 5171.62 - 25858.1 Torr; for 21.5 h;
Steps:
1 Synthesis of N-Methylglucamine
A 160 ml Parr reactor was charged with Raney nickel (2.7 g, 15 wt % based on D-glucose, Grace 4200) and water (20 g). The reactor was sealed, purged three times with 300 PSI N2 followed by three times with 300 PSI H2. The reactor was then charged with 300 PSI H2, at which point stiffing was begun at 400 RPM, and heated to 100-110° C. for 1 hr. The reactor and contents were cooled to 10° C. with external cooling; stir rate was slowed to 100 RPM and vented to 100 PSI. Next D-glucose was added (45 g 40% aqueous solution, 100 mmoles, Amresco) followed by methyl amine (15.37 g 40% aqueous solution, 150 mmoles, Aldrich) via an HPLC pump at 5 ml/min while maintaining a temperature of around 10° C. Reactor was charged to 450 PSI H2, stir rate was increased to 400 RPM and allowed to warm to ambient temperature over 30 min. The reactor was then externally heated to 35° C. for 18 hrs, 50° C. for 1 hr, 75° C. for 1 hr and finally 100° C. for 1 hr during which time pressure was maintained at 300-500 PSI H2. The reactor was cooled to ambient temperature, vented and purged three times with 300 PSI N2. The contents were filtered and stripped of water under reduced pressure on a rotary-evaporator at 70° C. The resultant solid was dissolved in refluxing methanol (35 ml) and allowed to stand at ambient temperature 18 hrs to yield a white solid, which was filtered and dried to yield 12.2 g (62.5% yield); GC Analysis was conducted by derivatizing 2 mg analyte in pyridine (1.5 ml, Aldrich BioTech Grade) with 99:1 BSTFA+TMCS (0.5 ml, Supelco, Sylon BFT) at 70-80° C. for 30 min. The retention time of material matched standard from Aldrich, and showed 99% pure product by area percent.
References:
US2014/255330,2014,A1 Location in patent:Paragraph 0207
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