Benzylethanolamine → Ammonia

Participants

Reaction Steps

A suspension of 4-imidazolecarboxaldehyde (14 g, 145.7 mmol) and N-benzylethanolamine (26.4 g, 174.8 mmol) in tetrahydrofuran (200 mL) was stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (37.06 g, 174.8 mmol) was added portionwise over 40 minutes, and the reaction stirred at room temperature for 18 hours. The reaction was quenched by the addition of water (150 mL), the mixture neutralised using saturated sodium bicarbonate solution, and then extracted with dichloromethane (3×300 mL). The combined organic extracts were dried (MgSO4) and evaporated under reduced pressure to give a yellow oil. This was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (95:5:0 to 90:10:1) to afford the title compound, 18.1 g.

Provenance & Evidence