SETT ATT FRAMSTELLA 1,3,4-TRIMETYL-2-(3,4,5-TRIMETOXIBENSYL)-1,2,5,6-TETRAHYDROPYRIDIN

• Main Authors: ROLADAN C M, JARQUE R G, PEINADO F R, CABIRO J C, CARTES J B
• Format: Patent
• Language: Swedish
• Published: 05.11.1975
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; ORGANIC CHEMISTRY; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES; SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS

A process for the preparation of 1,3,4-trimethyl-2- (3,4,5-trimethoxybenzyl) -1,2,5,6-tetrahydropyridine of the formula (I) ** (see formula) ** And its salts by addition of pharmaceutically acceptable acids, for example the hydrohates, characterized in that in a first stage of synthesis the 3,4,5-trimethoxybenzaldehyde of the formula is reacted ** (see formula) ** With the 2-bromo-3,4-dimethylpyridine of the formula: ** (see formula) ** Said reaction being carried out in solution in an inert solvent and in the presence of butyllithium at a reaction temperature comprised between -40ºC and room temperature, whereby 3,4,5-trimethoxyphenyl- is obtained as an intermediate product. (3,4-dimethyl-2-pyridyl) carbinol of the formula ii ** (see formula) ** Which in a second stage of synthesis is reacted at a temperature below 20ºC with thionyl chloride, and the chloride thus obtained dissolved in glacial acetic acid is reduced with zinc powder giving a product that treated with methyl iodide originates the iodide of 1,3,4-trimethyl-2- (3,4,5-trimethoxybenzyl) -pyridinium, which is treated with boron tetrahydride and sodium leads to the compound of formula i, which if desired is transformed into its salts of addition with pharmaceutically acceptable acids, for example the halohydrates. (Machine-translation by Google Translate, not legally binding)