ChemicalBook CAS DataBase List (+/-)-6-Methylnicotine

(+/-)-6-Methylnicotine synthesis

9synthesis methods

Product Name:(+/-)-6-Methylnicotine
CAS Number:101540-79-8
Molecular formula:C11H16N2
Molecular Weight:176.26

50-00-0 Synthesis

50-00-0
865 suppliers
$10.00/25g

90872-72-3 Synthesis

90872-72-3
55 suppliers
$187.91/250mg

101540-79-8
20 suppliers
$110.00/2mg

Yield:101540-79-8 276 g

Reaction Conditions:

in methanol at 50;

Steps:

1.4; 2

(4) 295g of 2-methyl-5-(pyrrolidin-2-yl)pyridine obtained in step (3), after dissolving with 600ml methanol, add 127g paraformaldehyde,The temperature was raised to 50°C, and the completion of the reaction was monitored by LC-MS. After 7 hours, the reaction was completed, and methanol and paraformaldehyde were distilled off under reduced pressure at 50°C.Add 500ml of 40% sodium hydroxide aqueous solution to adjust the pH to -11, extract three times with 1.5L ethyl acetate, and recover ethyl acetate by distillation under reduced pressure at 40°C.To obtain 2-methyl-5-(1-methylpyrrolidin-2-yl)pyridine, add 500ml of 18% hydrochloric acid aqueous solution, and extract twice with 600ml of petroleum ether,Keep the water phase, lower the temperature to -15°C, add solid sodium hydroxide to the water phase to adjust the pH to 12, extract three times with 1L ethyl acetate,Wash twice with saturated 1L sodium chloride aqueous solution, dry the organic phase over anhydrous sodium sulfate, and recover ethyl acetate by distillation under reduced pressure at 40°C.Afterwards, at 0.95Mpa, 140°C vacuum distillation gave 276g of pure 2-methyl-5-(1-methylpyrrolidin-2-yl)pyridine.The GC purity is 99.3%, and the total yield is 58.78% based on 6-methylnicotinic acid methyl ester.Fig. 1 is the 1HNMR spectrum of the obtained product. Figure 2 is the chiral analysis data of the product. Through chiral analysis, the ratio of R and S configurations is close to 1:1, so it is a racemate.

References:

CN114989135,2022,A Location in patent:Paragraph 0035; 0039-0041

5470-70-2 Synthesis