Borane;tetrahydrofuran → HCID 66858189, compound

Participants

Reaction Conditions

Reaction Steps

N-(4-Methoxy-2-nitro-phenyl)-2-[4-(4-methoxy-3-trifluoromethyl-phenyl)-piperazin-1-yl]acetamide (6.1 g; 11 mmol) iss dissolved in 70 ml tetrahydrofurane. Borane-tetrahydrofurane complex (90 ml of 1M THF solution) is added at 10° C. and the mixture is warmed to 55° C. for 4 hours. After cooling to room temperature, the solvent is evaporated under vacuum and the residue is taken with ethanol and acidified with hydrochloric acid. Heating to 50° C. takes place for 60 min. Upon overnight cooling, the unreacted compound is separated by filtration. The liquid phase is dried under vacuum, taken up with water and, after removal of the undissolved solid, saturated sodium hydrogencarbonate solution is added. The aqueous phase is extracted with ethylacetate and the organic layer is dessicated prior to evaporation. The residue is purified by silicagel chromatography (methylene chloride/methanol/32% aqueous ammonia 95:5:0.5). The title compound can be directly used for the following step.

Provenance & Evidence