Triethylamine → HCID 21993789, compound

Participants

Reaction Steps

To a suspension of 4.21 g (24.03 mmol.) of N-tert-butoxycarbonyl glycine and 5.51 g (35.98 mmol.) of 1-hydroxybenzotriazole monohydrate in acetonitrile (30 ml) was added, at room temperature, 6.90 g (36.0 mmol.) of N-ethyl-N′-3-(N,N-dimethylamino)propylcarboxiimide hydrochloride. The mixture was stirred for one hour. To the reaction system was then added a solution of 7.00 g (24.03 mmol.) of 4-amino-1-(3-phenylpropan-1-yl)piperidine dihydrochloride, 7.32 g (48.08 mmol.) of 1,8-bicyclo[5.4.0]unde-7-cene (DBU) and 3.4 ml (24.4 mmol.) of triethylamine in acetonitrile (20 ml). The mixture was stirred for 2 hours at room temperature. The solvent was distilled off under reduced pressure. To the residue was added chloroform. The mixture was washed with water and a saturated aqueous saline solution, followed by drying over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by means of a column chromatography (methanol/ethyl acetate 30%). The solvent was distilled off under reduced pressure to give the object compound as a yellowish orange liquid product. The yield was 5.35 g (59%).

Provenance & Evidence