Tetrahydrofuran → HCID 178457166, compound

Participants

Reaction Steps

To the solution of 10.9 g of 2-methyl-6-hydroxypyridine in 400 ml of tetrahydrofuran, 88 ml of 2.5 molar n-butyllithium in hexane are added dropwise while stirring under nitrogen at 0°. After 2 hours 10.2 g of 1-isopropyliminoethane are added rapidly and the mixture stirred for 2 hours at 0°. It is poured into 200 ml of saturated aqueous ammonium chloride, the organic layer separated and the aqueous solution extracted 4 times with 150 ml of methylene chloride. The combined organic solutions are dried, filtered, evaporated and the residue is chromatographed on 300 g of silica gel with methanoldiethyl ether (5:1) as moving phase. The eluate is evaporated, the residue taken up in ethanol, neutralized with ethanolic fumaric acid and the resulting precipitate recrystallized from ethanol, to yield the mono-fumarate of N-[2-(6-hydroxy-2-pyridyl)propyl]-isopropylamine of Formula II, with R=OH, R'=H and CpH2p±1 =CH(CH3)2, melting at 193.5°-194°.

Provenance & Evidence