Benzamidine → HCID 178422219, compound

Participants

Reaction Steps

A solution of acetal (2) (1 g, 5.02 mmol), benzamidine (786 mg, 5.02 mmol), and DBU (1.5 mL, 10.04 mmol) in dry DMF (15 mL) was heated to 85° C. for 15 h. The mixture was diluted with CHCl3 (30 mL) and washed with 0.5 N NaOH (10 mL) and H2O (20 mL). The organic fraction was dried, filtered and concentrated to a brown oil. Flash chromatography (SiO2; 1/9 EtOAc/CH2Cl2, Rf 0.35) was attempted, but material crystallized on the column. The silica gel was washed with MeOH. Fractions containing the product (3) were concentrated and used without further purification (783 mg, 54.3%):

Provenance & Evidence