Sodium Iodide → HCID 117856688, compound

Participants

Reaction Steps

(S)-Piperidin-3-yl-carbamic acid tert-butyl ester (150 mg), 4-benzyloxybenzyl chloride (383 mg), K2CO3 (227 mg) and NaI (34 mg) are stirred in dimethylsulfoxide (5 mL) for 16 h. Volatiles are evaporated in vacuo, the residue partitioned between water and ethyl acetate, the organic phase collected, dried (Na2SO4) and volatiles evaporated in vacuo to give 540 mg of crude product that is used without further purification. To the material thus obtained dichloromethane (15 mL) and trifluoroacetic acid (0.56 mL) are added. After 16 h at room temperature volatiles are evaporated in vacuo, methanolic NH3 is added until a slightly basic pH is reached, volatiles are again evaporated and the residue is purified by chromatography (silica gel, dichloromethane:MeOH containing NH3OH gradient of increasing polarity) to give the title compound. Yield 110 mg.

Provenance & Evidence