Hydrochloric Acid → Pirmagrel

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Reaction Steps

The residue is partitioned between water and methylene chloride after pH is adjusted to 10. The aqueous solution is further washed with chloroform, acidified to pH 1 and again washed with ether and toluene. After pH is adjusted to 5.5, extraction with chloroform gives crude 5-(5-carboxypentyl)imidazo-[1,5-a]pyridine. A solution of the acid in 30 ml of acetonitrile is treated with 5N ethanolic hydrochloric acid. After addition of 25 ml of ethyl ether, 5-(5-carboxypentyl)imidazo[1,5-a]pyridine hydrochloride, melting at 201°-4°, crystallizes. 5-(5-Carboxypentyl)-imidazo[1,5-a]pyridine (example 2) is obtained on neutralization of a methanolic solution of the salt to pH 5.

Provenance & Evidence