Acrolein → HCID 22676614, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-benzylpiperidine (3.51 g) in 40 ml of tetrahyfrofuran, 1,8-diazabicyclo[5.4.0]-7-undecene (0.03 ml) was added and the mixture was cooled at −20° C. Acrolein (1.485 ml) was added dropwise for 10 min and the mixture was stirred for 1 h at −20° C. 3-Aminopyridine (1.88 g) and sodium triacetoxyborohydride (8.48 g) were added and the mixture was stirred at room temperature for 15 h. 1N NaOH (120 ml) was added and stirred for 1 h. The reaction mixture was extracted with ethyl ether (60 ml) 3 times. The combined organic layer was washed with brine (50 ml), dried over anhydrous MgSO4. After concentration, the residue was purified on silica gel column chromatography (AcOEt-methanol 3:1) to give the title compound (2.34 g, yield 37.8%).

Provenance & Evidence