Trifluoroacetic acid → HCID 20232515, compound

Participants

Reaction Steps

A solution of N—BOC-piperazine (4.3 g) and triethylamine (9 ml) in dimethylsulfoxide (40 ml) at 0° C. under nitrogen was treated with 4-chlorocinnamyl chloride (5 g) and the resulting solution was stirred at room temperature for 18 hours, poured into water, extracted with ethyl acetate (three times), dried over sodium sulfate and concentrated in vacuo. The residue was filtered over silica gel to afford crude 4-[(E)-3-(4-Chloro-phenyl)-allyl]-piperazine-1-carboxylic acid tert-butyl ester. This compound was dissolved in dichloromethane (30 ml) and treated with trifluoroacetic acid (10 ml) at room temperature for 18 hours. Concentration afforded 1-[(E)-3-(4-Chloro-phenyl)-allyl]-piperazine (5.8 g), which was characterised by its mass and NMR spectra. MS (ES+) 151/153 (M-piperazine), 237/239 (M+H+).

Provenance & Evidence