Furfurylamine → 1-(Furan-2-yl)-N-[(thiophen-2-yl)methyl]methanamine

Participants

Reaction Steps

A mixture of furfurylamine (2.0 g, 0.0206 mol) and 2-thiophenecarboxaldehyde (2.31 g, 0.0206 mol) in dichloromethane (60 ml) was stirred at room temperature for 5 minutes before adding portionwise sodium triacetoxyborohydride (5.24 g, 0.0247 mol). After addition was complete (approx. 2 minutes), the reaction mixture was stirred at room temperature for 3 hours and washed with sat'd NaHCO3 (aq.), dried (MgSO4), filtered and concentrated. The product mixture was purified by flash chromatography (silica gel 60, 230-400 mesh, 4:1 hexanes:EtOAc to 1:1 hexanes:EtOAc) to obtain the amine as a light yellow oil, 1.65 g (41%). MS (APCI): (M+1)+=194; 1H-NMR is consistent with structure.

Provenance & Evidence