N-Hydroxysuccinimide → HCID 21993721, compound

Participants

Reaction Steps

To a suspension of 1.0 g (4.58 mM) of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid and 0.90 g (7.82 mM) of N-hydroxysuccinimide in acetonitrile (10 ml) was added 1.51 g (7.88 mM) of N-ethyl-N′-3-(N,N-dimethylamino)propylcarbodiimide hydrochloride at room temperature, and the mixture was stirred for 1 hour. To this reaction mixture was added a solution of 1.67 g (4.73 mM) of 1-[4-(aminomethyl)benzyl]-4-phenylpiperidine dihydrochloride, 1.44 g (9.46 mM) of DBU, and 0.55 ml (3.95 mM) of triethylamine in acetonitrile (20 ml), and the mixture was further stirred for 4 hours. The solvent was then distilled off under reduced pressure and the residue was diluted with water and extracted with ethyl acetate (a small amount of ethanol was additionally used). The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. This crude product was purified by column chromatography (methanol/ethyl acetate 20-30%) to provide the title compound as red amorphous substance.

Provenance & Evidence