Triethylamine → HCID 67141134, compound

Participants

Reaction Steps

To (S)-(−)-oxo-1,5-imidazolinedicarboxylic acid 1-benzylester (10 g) and 1-(2,5-dimethylphenyl)-piperazine (7.92 g) in N,N-dimethylformamide was added O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N,N-tetra-methyluronium-tetrafluorborate (TPTU) (12.36 g) and triethylamine (15.8 mL), and the reaction mixture was stirred at ambient temperature over night. Additional amounts of the reagents were added, 1-(2,5-dimethylphenyl)-piperazine (1.44 g), TPTU (2.25 g) and triethylamine (2.9 mL), and stirring was continued until no starting material could be detected. The solvent was evaporated and the residue redissolved in ethyl acetate/1M aqueous solution of Na2CO3. The inorganic phase was extracted with ethyl acetate and the combined organic phases were dried (Na2SO4), filtered and evaporated. Purification by column chromatography (SiO2, dichloromethane/methanol 95:5) yielded (S)-5-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-2-oxo-imidazolidine-1-carboxylic acid benzyl ester (14.4 g) as a white solid. MS: 435.3 ([M−H]−)

Provenance & Evidence