Hydrochloric Acid → HCID 131721293, compound

Participants

Reaction Conditions

Reaction Steps

9.5 g (37.9 mmoles) of N-(3-diethylaminopropoxy)-3-pyridinecarboxamidine are added under stirring to the mixture of 65 ml of distilled water and 21.7 ml of concentrated hydrochloric acid, cooled to 0° C. To the yellow solution, 13.08 g (189.5 mmoles) of sodium nitrite dissolved in 54 ml of distilled water are dropwise added at -5° C. during 50 minutes, then the reaction mixture is stirred at a temperature of -5° C. for 2 hours. Subsequently, the pH of the solution is adjusted to 11 by adding 2N sodium hydroxide solution, and the mixture is extracted 3 times with 70 ml of chloroform each. The organic phase is washed with 30 ml of water, dried over sodium sulfate and evaporated. The residue is purified by column chromatography (adsorbent: Merck Kieselgel 60; eluent: chloroform/methanol 1:1). The base obtained in a yield of 5.17 g (50.6%) is transformed by adding methanolic solution of hydrogen chloride to obtain the title hydrochloride, m.p.: 152-153° C.

Provenance & Evidence