Sodium Iodide → HCID 178464459, compound

Participants

Reaction Steps

A solution of 293 mg (corresponds to 0.5 mmol) of trans-Methanesulfonic acid 3-{4-[methyl-(4-trifluoromethyl-phenoxycarbonyl)-amino]-cyclohexyl}-propyl ester in 2.5 ml of DMA was cooled to 0° C., treated with 0.195 ml (2 mmol) of Ethyl-(2-hydroxy-ethyl)-amine and stirred over night at RT. A catalytic amount of NaI and 0.195 ml (2 mmol) of Ethyl-(2-hydroxy-ethyl)-amine and after 9 h, 0.88 ml (1 mmol) of Ethyl-(2-hydroxy-ethyl)-amine were added. After 16 h, the solvent was evaporated and the residue extracted with aqueous saturated NaHCO3/Et2O (3×). The organic phase was dried with Na2SO4, filtered and evaporated. Purification by flash column chromatography on silica gel (CH2Cl2/MeOH 9:1) gave 48 mg (22%) of pure trans-(4-{3-[Ethyl-(2-hydroxy-ethyl)-amino]-propyl}-cyclohexyl)-methyl-carbamic acid 4-trifluoromethyl-phenyl ester, MS: 431 (MH+). The following compounds were prepared in analogy:

Provenance & Evidence