Benzylamine → HCID 178420324, compound

Participants

Reaction Steps

Benzimidazol-5-carbaldehyde (146 mg; 1 mmol; 1 eq.) was dissolved in MeOH (10 ml). Benzylamine (0.109 ml; 1 mmol; 1 eq.) was added and the mixture was stirred overnight. NaBH4 (57 mg; 1.5 mmol; 1.5 eq.) was added and stirring was continued overnight. The reaction was quenched by addition of water and extracted with ethyl acetate (3×25 ml). The combined organic layers were dried over Na2SO4 and evaporated. The residue was purified by flashchromatography on silica using a CHCl3/MeOH gradient. Yield: 0.045 g (19%); MS m/z: 238.4 [M+H]+; 1H-NMR (400 MHz, DMSO d6): δ 3.65 (s, 2H); 3.74 (s, 2H); 7.10-7.20 (m, 2H); 7.25-7.32 (m, 4H); 7.40-7.55 (m, 2H); 8.11 (s, 1H); 12.28 (br s, 1H); HPLC (METHOD [A]): rt 4.98 min (95.0%)

Provenance & Evidence