Pyridine → HCID 57267718, compound

Participants

Reaction Steps

Under nitrogen, a solution of (2S)-1-[N-(3-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-benzylamino]-3-phenoxy-2-propanol (150 mg), benzoyl chloride (44 μl), pyridine (35 μl), and catalytic amounts of 4-dimethylaminopyridine in dichloromethane (5 ml) was stirred at room temperature for 5 hours. The resulting mixture was poured into saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) to give N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]-3-benzoylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamine (163 mg).

Provenance & Evidence