Mechlorethamine → 3-(4-Fluorophenyl)-5-methyl-1-(1-methylpiperazin-4-yl)-1H-indole

Beteiligte Stoffe

Reaktionsschritte

To a mixture of 1-amino-3-(4-fluorophenyl)-5-methyl-1H-indole 19a (1 g) and toluene (20 ml) was added a 50% suspension of sodium amide in xylene (1.0 ml). After reaction for 15 min at room temperature a solution of N,N-bis(2-chloroethyl)methylamine (0.8 g) in toluene was added slowly and the mixture was refluxed for 3 h. After cooling to room temperature, the solvents were evaporated in vacuo and water (100 ml) was added. The mixture was extracted with ethyl acetate (2×50 ml) and the combined organic phases were dried (Na2SO4). Evaporation of the solvents in vacuo afforded the title compound, which was purified by column chromatography on silica gel (eluted with ethyl acetate/ethanol 4:1 containing 4% triethylamine) and crystallized from heptane. Yield: 0.5 g, mp 105°-107° C.

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