N,N-dimethyl-1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-4-amine → 1-(2-amino-4-(trifluoromethyl)phenyl)-N,N-dimethylpiperidin-4-amine

HRID 502728Notes

Reaction equation

HRID 502728 reaction equation
[CH3:1][N:2]([CH3:22])[CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=2[N+:19]([O-])=O)[CH2:5][CH2:4]1>[Pd].CO>[NH2:19][C:10]1[CH:11]=[C:12]([C:15]([F:16])([F:17])[F:18])[CH:13]=[CH:14][C:9]=1[N:6]1[CH2:5][CH2:4][CH:3]([N:2]([CH3:22])[CH3:1])[CH2:8][CH2:7]1

Participants

4

Reactant 1

HCID 16109041N,N-dimethyl-1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-4-amine

Product 1

HCID 161090251-(2-amino-4-(trifluoromethyl)phenyl)-N,N-dimethylpiperidin-4-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To N,N-dimethyl-1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-4-amine (3.4 g, 11 mmol) was added Pd/C (10%, 0.57 g) under nitrogen. Methanol (25 mL) was added via syringe, and H2 gas was introduced and the mixture stirred vigorously under an atmosphere of H2. After 96 h, the mixture was flushed with nitrogen, filtered through celite and concentrated. The residue was resubjected to the reaction conditions. After 12 h, the reaction was flushed with nitrogen, filtered through celite and concentrated. The resulting solid was triturated with methanol ten times to give the title compound as a pink solid. MS (m/z): 288.2 (M+H)+. Calc'd for C14H20F3N3: 287.32.

Workup

  1. additionH2 gas was introduced
  2. customthe mixture was flushed with nitrogen
  3. filtrationfiltered through celite
  4. concentrationconcentrated
  5. customThe residue was resubjected to the reaction conditions
  6. waitAfter 12 h
  7. customthe reaction was flushed with nitrogen
  8. filtrationfiltered through celite and
  9. concentrationconcentrated
  10. customThe resulting solid was triturated with methanol ten times

Sources & evidence

ORD record
ord-2f4e796704884fadb851981b70e64c57
Source dataset
uspto-grants-2010_08
Patent number
US07776869B2

Reaction notes

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