Acetic Acid → N-Butyl-3-pyridinamine

To a solution of 941 mg (10 mmol) of 3-aminopyridine and 0.9 mL of butyraldehyde in 30 mL of CH3OH was added 10 mL of glacial acetic acid. The mixture was stirred at room temperature for 1 hour, then the reaction was cooled with an ice bath, and 650 mg (10.3 mmol) of sodium cyanoborohydride was added. The ice bath was removed, and the reaction was stirred for 4.5 hours at room temperature. The mixture was poured into 300 mL of 0.67M NaOH(aq.), and extracted with ethyl acetate (3×50 mL). The combined organic layers were back extracted with brine (1×50 mL), dried over MgSO4, filtered, and concentrated to an oil. The product was isolated via silica gel chromatography, eluting with 3:1 ethyl acetate:hexanes to give 1.18 g (79%) of a colorless solid.

1. temperaturethe reaction was cooled with an ice bath
2. customThe ice bath was removed
3. stirringthe reaction was stirred for 4.5 hours at room temperature
4. additionThe mixture was poured into 300 mL of 0.67M NaOH(aq.)
5. extractionextracted with ethyl acetate (3×50 mL)
6. extractionThe combined organic layers were back extracted with brine (1×50 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated to an oil
10. customThe product was isolated via silica gel chromatography
11. washeluting with 3:1 ethyl acetate

ORD record

ord-f1ea28350f8b472cbef2bb47042d2521

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07365093B2