[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:21]([O-])=O)=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH2:11][CH2:10]2)[CH:7]=1.C([O-])=O.[NH4+]>[Pt].CO>[NH2:21][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][C:6]=1[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH2:13][CH2:14]1688 mg (0.0018 mol, 1 eq) of N-(5-bromo-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine D10, 350 mg (0.00018 mol, 0.1 eq) of 10% platinum on carbon, 375 mg (0.0057 mol, 3.2 eq) of ammonium formate, and 20 mL of methanol (degassed with nitrogen) were combined and stirred for 1 hour. The catalyst was then filtered off, and the filtrate was evaporated. Water and dichloromethane were added and shaken. Separation and drying of the dichloromethane layer with sodium sulfate followed by evaporation yielded a crude product which was purified exactly as in Example 1 where A=H2O and B=CH3CN to yield (2-amino-5-bromophenyl)[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]amine, the title compound. MS (ESI): 355 [M+H]+.
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