Benzaldehyde → HCID 58852302, compound

Participants

Reaction Conditions

Reaction Steps

In a small pressure bottle was placed 4-(2-amino-4-methyl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester, benzaldehyde (92 μL, 0.90 mmol), sodium hydrogensulfite (147 mg, 1.48 mmol) in DMF (5 mL). The bottle was sealed and heated at 100° C. for two hours and then stirred at 25° C. overnight for 16 hours. The reaction mixture was then concentrated in vacuo and partitioned between ethyl acetate (15 mL) and brine/water (1:1, 15 mL). The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. Flash chromatography (Biotage 40S column, 40/60 ethyl acetate/hexanes) afforded 4-(5-methyl-2-phenyl-benzoimidazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (339 mg, quantitative) as a light purple foam.

Provenance & Evidence