Sodium hydride → HCID 68502153, compound

Participants

Reaction Steps

The solution of 0.155 g of benzyl 3-(1H-indol-6-ylmethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 1.5 ml of DMPU is admixed with stirring at room temperature with 0.015 g of sodium hydride dispersion (60%). The mixture is stirred over 5 minutes and subsequently admixed with 0.081 ml of 1-chloro-3-methoxypropane and 0.007 g of tetrabutylammonium iodide. The reaction mixture is stirred at room temperature over 24 hours, cooled and poured onto water (20 ml). The mixture is extracted with tert-butyl methyl ether (2×20 ml). The organic phases are washed successively with water (2×20 ml) and brine (1×20 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as an orange oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.25 (1:1 EtOAc-heptane); Rt=27.51 (II).

Provenance & Evidence