Ammonium formate → (2-amino-5-bromophenyl)[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]amine

HRID 2064057Notes

Reaction equation

HRID 2064057 reaction equation
[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]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59863010N-(5-bromo-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine

Product 1

HCID 59863030(2-amino-5-bromophenyl)[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]amine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

688 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]+.

Workup

  1. filtrationThe catalyst was then filtered off
  2. customthe filtrate was evaporated
  3. additionWater and dichloromethane were added
  4. stirringshaken
  5. customSeparation
  6. dry with materialdrying of the dichloromethane layer with sodium sulfate
  7. customfollowed by evaporation
  8. customyielded a crude product which
  9. customwas purified exactly as in Example 1 where A=H2O and B=CH3CN

Sources & evidence

ORD record
ord-c5846354863743cda88c2640ede245e9
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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