Sodium Hydroxide → Lifarizine

Participants

Reaction Steps

One mole of 4-hydroxymethyl-2-(4-methylpheny)-5-methyl-1H-imidazole (202 g) was dissolved in 2 liters of 95% ethanol, then 252 g (1 mole) of N-(diphenylmethyl)piperazine was added portionwise. This was followed by the addition of 1 liter of water, 60 g (1.5 mole) of sodium hydroxide (as 12N solution) and 8.7 g (0.1 mole) of lithium bromide. The reaction medium was refluxed for 5 hours, allowed to cool to room temperature, and was stirred overnight. The precipitate that formed was filtered and purified by reslurrying from 1.2 liters of an ethanol-water mixture (60/40) to produce the 383.6 g of the title compound (0.88 mole, 88% yield), having a melting point of 238° C.

Provenance & Evidence