Sodium hydride → Benzyl 3-[7-bromo-1-(3-methoxypropyl)-3-methyl-1H-indol-6-yl methoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Participants

Reaction Steps

The solution of 0.208 g benzyl 3-(7-bromo-3-methyl-1H-indol-6-ylmethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 2.0 ml of N,N-dimethylformamide is cooled to 0° C., admixed with 0.023 g of sodium hydride dispersion (60%) and stirred over 10 minutes. The mixture is admixed successively with 0.126 ml of 1-chloro-3-methoxypropane and 0.011 g of tetrabutylammonium iodide and subsequently stirred at room temperature over 18 h. The reaction mixture is poured onto 1M sodium hydrogencarbonate solution (30 ml) and extracted with tert-butyl methyl ether (2×30 ml). The organic phases are washed with water (30 ml) and brine (30 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.17 (1:2 EtOAc-heptane); Rt=6.60.

Provenance & Evidence