Propylamine → 2-(Propylamino)-1-(pyridin-3-yl)ethanol

Participants

Reaction Conditions

Reaction Steps

To 1.01 g (3.6 mmol) of 3-bromoacetylpyridine hydrobromide, prepared as described in Example 1, was added 20 ml of absolute ethanol and 0.5 g (13.2 mmol) of sodium boronhydride (NaBH4). The reaction mixture was stirred at 20° C. for 2 hours and filtered. To the filtrate containing 3-pyridyloxirane was added 0.7 ml (8.5 mmol) of n-propylamine and heated at reflux temperature of the reaction mixture for 5 hours. The reaction mixture was then evaporated to a dry residue and to it was added 20 ml of chloroform, a solid portion was filtered off, the filtrate was evaporated and an oil residue formed was purified by column chromatography on silica gel (silica gel 60, mobile phase: CHCl3:ethyl acetate=10:2). This yields 0.33 g (50%) of 1-(3-pyridyl)-2-propylaminoethanol in the form of the oil base (molecular weight: 180.25, gross formula: C10H16N2O)

Provenance & Evidence