Dichloromethane → HCID 66854859, compound

Participants

Reaction Steps

A solution of 4-(5-fluoro-2-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl ester (10 g, prepared from 2,4-difluoronitrobenzene as described in Example 1, Step A) in dichloromethane (80 ml) was treated with trifluoroacetic acid (23 ml) for 24 hours at room temperature. The reaction mixture was concentrated in vacuo. The residue was dissolved in acetonitrile (100 ml), diisopropylethylamine (27 ml) and 4-chloro-cinnamyl chloride (6.8 g) were added. The solution was stirred for 17 hours at room temperature, the solvent was removed in vacuo and the residue was subjected to silica gel chromatography (cyclohexane:ethyl acetate 1:1) to afford 1-[(E)-3-(4-chloro-phenyl)-allyl]-4-(5-fluoro-2-nitro-phenyl)-piperazine (10.5 g); 1H NMR (400 MHz, CDCl3) 2.7 (t, J=8 Hz, 4H), 3.1 (t, J=8 Hz, 4H), 3.2 (d, J=9 Hz, 2H), 6.2 (dt, J=18, 9 Hz, 1H), 6.5 (d, J=18 Hz, 1H), 6.6 (dt, J=1.0, 7.0 Hz, 1H), 6.7 (dd, J=1.0, 10 Hz, 1H), 7.2-7.3 (m, 4H), 7.8 (d, J=7.0, 10.0 Hz, 1H); MS (ES+) 151/153, 376/378 (M+H+).

Provenance & Evidence