Phenethylamine → [1-(3-Fluoro-4-phenethylcarbamoyl-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

Participants

Reaction Steps

Thionyl chloride (0.16 g, 2.2 mmol) was added dropwise to a stirred solution of 4-(4-tert-butoxycarbonylamino-piperidine-1-sulfonyl)-2-fluoro-benzoic acid (0.3 g, 0.75 mmol) and pyridine (0.36 ml, 4.5 mmol) in DCM (10 ml). The reaction mixture was stirred at room temperature under a nitrogen atmosphere for 4 hours, after this time phenethylamine (0.19 ml, 1.5 mmol) was added in one portion and stirring was continued for a further 12 hours. The mixture was then diluted with DCM (10 ml) before being washed sequentially with HCl (1M solution, 10 ml) and NaOH (1M solution, 10 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated to give the title compound (0.38 g, 74%) as a white foam which was taken on without further purification. Tr=2.16 min m/z (ES+) (M+Na+) 528.

Provenance & Evidence