Ethanol → Latrepirdine

Participants

Reaction Conditions

Reaction Steps

Concentrated HCl (6 cm3) was added to EtOH (4 cm3). The crude N′-(1-methyl-piperidin-4-ylidene)-N-[2-(6-methyl-pyridin-3-yl)-ethyl]-N-p-tolyl-hydrazine was dissolved in this ethanolic HCl and heated to 100° C. for 30 minutes. The reaction was then cooled, and diluted with H2O (10 cm3), saturated with Na2CO3, and extracted with CHCl3 (3×50 cm3). The combined extracts were dried (MgSO4) and solvent removed. The residual brown oil was purified by flash column chromatography over SiO2 (10×2 cm) eluting with 1:1 EtOAc/MeOH to provide the desired product as a pale brown powder (612 mg, 63% yield over 3 steps based on last pure starting material (2-methyl-5-(N-nitroso-2-p-tolylaminoethyl)pyridine)).

Provenance & Evidence