1-(3-(Trifluoromethyl)phenyl)piperazine → 1,3-Dichloro-5-methoxy-2-{4-[3-(trifluoromethyl)phenyl]piperazinyl}benzene

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 2.5 grams (0.0096 mole) of 1,3-dichloro-5-methoxy-2-bromobenzene (known compound), 0.18 mL (0.0096 mole) of 1-(α,α,α-trifluoro-meta-tolyl)piperazine (known compound), 0.18 gram (0.0002 mole) of tris(dibenzylideneacetone)dipalladium(0), 0.36 gram (0.0006 mole) of racemic-2,2′-bis(diphenylphosphono)-1,1′-binaphthyl, and 1.66 grams (0.017 mole) of sodium tert-butoxide in 100 mL of toluene was heated at 100° C. for about 60 hours. After this time, the reaction mixture was cooled and washed with two 10 mL portions of water. The organic layer was dried with sodium sulfate, filtered, and concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using 1:3 and 1:1 mixtures of methylene chloride:hexane as eluants. The appropriate fractions were combined and concentrated under reduced pressure, yielding 2.1 grams of the subject compound, mp 87-89° C. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence