1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178523381, compound

Participants

Reaction Steps

To a solution of 0.41 g (1.88 mM) of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid and 0.37 g (3.21 mM) of N-hydroxysuccinimide in acetonitrile (5 ml) was added 0.62 g (3.23 mM) of N-ethyl-N′-3-(N,N-dimethylamino)propylcarbodiimide at room temperature, and the mixture was stirred for 1 hour. To this reaction mixture was added a suspension of 0.70 g (1.95 mM) of 1-(trans-4-aminomethyl-1-cyclohexylmethyl)-4-phenylpiperidine dihydrochloride and 1.0 ml (7.71 mM) of triethylamine in chloroform (10 ml) and the mixture was further stirred for 2 hours. The solvent was then distilled off under reduced pressure and the residue was diluted with water and a small amount of ethanol and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. After concentration, the crude product obtained was purified by column chromatography (methanol/ethyl acetate 30-50%) and recrystallization from ethyl acetate to provide the title compound as red-purple crystals.

Provenance & Evidence