[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([N+:16]([O-])=O)[CH:15]=1)[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]1.Cl>[Fe].CO>[F:1][C:2]1[CH:15]=[C:14]([NH2:16])[CH:13]=[C:4]([O:5][CH:6]2[CH2:7][CH2:8][N:9]([CH3:12])[CH2:10][CH2:11]2)[CH:3]=1Combine 4-(3-fluoro-5-nitro-phenoxy)-1-methyl-piperidine (preparation 16, 2.75 g, 10.82 mmol), iron dust (2.0 g, 35.69 mmol), methanol (150 mL) and 1M aqueous hydrochloric acid solution (3.25 mL, 3.25 mmol), stir and heat at reflux. After 32 hr., cool to ambient temperature, filter through celite and concentrate to an oil. Partition between ethyl acetate (100 mL) and 1M aqueous sodium hydroxide solution (50 mL), separate the organic layer, dry over sodium sulfate, filter and concentrate. Purify residue by silica gel flash chromatography eluting with 10% (2M NH3/methanol)/methylene dichloride to give the title compound (1.35 g, 56%). 1H NMR (CDCl3): 6.0 (m, 3H), 4.2 (m, 1H), 3.7 (bs, 2H), 2.7 (m, 2H), 2.3 (m, 5H), 2.0 (m, 2H), 1.8 (m, 2H).
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