Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][CH:7]=1.[CH3:13][C:14]1([CH3:20])[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[I:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:16]2[CH2:17][CH2:18][CH2:19][C:14]([CH3:20])([CH3:13])[CH2:15]2)=[CH:7][CH:8]=1A mixture of 1-[(3-chloropropyl)oxy]-4-iodobenzene (for example, as prepared for Intermediate 1) (6.5 g, 20 mmol), 3,3-dimethyl piperidine (commercially available, for example from Alfa) (3.39 g, 30 mmol), sodium iodide (2.99 g, 20 mmol) and potassium carbonate (3.3 g, 20 mmol) in anhydrous acetonitrile (100 ml) was heated at reflux overnight. The mixture was allowed to cool to room temperature, evaporated to dryness and quenched with water and extracted with dichloromethane, dried, filtered and concentrated to afford the title compound (8 g). LCMS RT=2.37 min, ES+ve m/z 374 (M+H)+.
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