alpha-[(2-pyridylamino)methyl]benzyl alcohol monohydrochloride

Analexin, Mallinckrodt Inc., US ,1960

Analgesic; relaxant (skeletal muscle).

A mixture containing 188 g (0.20 mol) of 2-arninopyridine, 0.55 g of lithium amide and 75 cc of anhydrous toluene was refluxed for 1.5 hours. Styrene oxide (12.0 g = 0.10 mol) was then added to the reaction mixture with stirring over a period of ten minutes. The reaction mixture was stirred and refluxed for an additional 3.5 hours. A crystalline precipitate was formed during the reaction which was removed by filtration, MP 170°C to 171°C. 1.5 g. The filtrate was concentrated to dryness and a dark residue remained which was crystallized from anhydrous ether; yield 6.0 g. Upon recrystallization of the crude solid from 30 cc of isopropyl alcohol, 2.0 g of a light yellow solid was isolated; MP 170° to 171°C.

Analgesic, Muscle relaxant