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

HRID 1042682Notes

Reaction equation

HRID 1042682 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-3ba691e596df49fd93e45b50cc062bb9
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

Loading…