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

Temperature

20 °C

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)

1. filtrationfiltered
2. additionTo the filtrate containing 3-pyridyloxirane
3. temperatureheated
4. temperatureat reflux temperature of the reaction mixture for 5 hours
5. customThe reaction mixture was then evaporated to a dry residue and to it
6. additionwas added 20 ml of chloroform
7. filtrationa solid portion was filtered off
8. customthe filtrate was evaporated
9. customan oil residue formed
10. customwas purified by column chromatography on silica gel (silica gel 60, mobile phase: CHCl3:ethyl acetate=10:2)

ORD record

ord-0b78a1d0a98643e4bcc4f27be197a0fa

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560474B2