[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH2:22][CH2:23][C:24]#[N:25]>C(#N)C>[C:24]([CH2:23][CH2:22][CH2:21][N:11]1[CH2:12][CH2:13][N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH2:9][CH2:10]1)#[N:25]2-Fluorophenyl piperazine (6.5 g) are suspended in acetonitrile (50 ml), anhydrous K2CO3 (1.5 eq) and 4-bromobutyronitrile (1.05 eq) in acetonitrile (25 mL) are added dropwise. The mixture is heated at reflux for 10 h and then filtered, the filtrate is concentrated in vacuo. The residue is taken up in AcOEt and washed three times with water. The organic layer is extracted with hydrochloric acid (1M) and the aqueous acid layer is washed with AcOEt and neutralized with aqueous ammonia (28% in H2O) to pH 11. The extraction is carried out with AcOEt and the organic layer is washed twice with water and dried over Na2SO4. The mixture is concentrated to give the title compound (8.35 g, 98%). 1H NMR (200 MHz, CDCl3) δ 1.80-1.90 (m, 2 H), 2.42-2.49 (m, 2H), 2.52-2.56 (m, 2H), 2.59-2.64 (m, 4H), 3.07-3.13 (m, 4H), 6.91-7.07 (m, 4H). RMN 13C (50 MHz, CDCl3): δ 14.8, 22.6, 50.4, 53.0, 56.2 115.8, 116.2 118.8, 119.7, 122.3, 122.5, 124.3, 124.4, 153.1, 158.0.
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