[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH2:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].F[C:14]1[CH:15]=[C:16]([CH3:23])[CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.CCCCCC>CN(C)C=O.O.C(OCC)(=O)C.[I-].[K+]>[CH3:23][C:16]1[CH:15]=[CH:14][C:19]([N+:20]([O-:22])=[O:21])=[C:18]([NH:12][CH:9]2[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH2:10]2)[CH:17]=1Ethyl-4-amino-1-piperidine-carboxylate (18.3 g, 106 mmol) was added to a stirred suspension of 3-fluoro-4-nitrotoluene (15.0 g, 97 mmol), sodium carbonate (10.3 g, 97 mmol) and potassium iodide (0.16 g, 0.97 mmol) in dimethylformamide (150 mL). The mixture was heated to 50° C., stirred for 15 hours and then allowed to cool. The reaction mixture was diluted with water (200 mL) and ethyl acetate (200 mL). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (2×200 mL). The organic extracts were combined, extracted with a 10% aqueous solution of citric acid (250 mL), dried over MgSO4 and evaporated under reduced pressure. The residue was purified by column chromatography on silica, eluting with dichloromethane and then ethyl acetate/hexane (7:8) to give the title compound (25.0 g, 84% yield) as a yellow solid. (Rf: 0.3 (ethyl acetate/hexane 7:8))
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