[Br:1][C:2]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]#[N:12])[CH2:7][CH2:6]1.Cl.[NH2:19][OH:20].C([O-])([O-])=O.[Na+].[Na+]>CCO.O>[Br:1][C:2]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11](=[N:19][OH:20])[NH2:12])[CH2:7][CH2:6]1A mixture of 4-(2-bromo-5-fluorophenoxy)piperidine-1-carbonitrile (1.6 g, 5.3 mmol), hydroxylamine hydrochloride (1.1 g, 16.1 mmol) and Na2CO3 (2.3 g, 92 mmol) in EtOH/water 4:1 (26 ml) was heated at 80° C. for 1 h. The solvent was evaporated. The residue was acidified with 6N HCl and washed with Et2O (2×10 mL). The aqueous layer was made basic with solid Na2CO3 and extracted with EtOAc (3×20 mL). The combined organic fractions were dried over Na2SO4 and the solvent was evaporated under reduced pressure to give the title compound as a foam which was used in the next step without further purification. MS: m/z 332, 334 (MH+).
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