[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][CH2:10]Cl.Cl.[F:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][CH2:10][N:17]1[CH2:18][CH2:19][CH:14]([F:13])[CH2:15][CH2:16]1A mixture of 1-bromo-2-(2-chloroethoxy)benzene (2.35 g), 4-fluoropiperidine hydrochloride (1.54 g), potassium carbonate (4.06 g) and potassium iodide (0.83 g) in dimethylformamide (20 ml) was heated at 80° C. for 18 h. After evaporation, the residue was partitioned between ethyl acetate and water. The solvent phase was washed (brine), dried and evaporated to give an oil (1.0 g).
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