(S)-N,N-dimethyl-1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-amine → (S)-1-(2-amino-4-(trifluoromethyl)phenyl)-N,N-dimethylpiperidin-3-amine

HRID 446251

Reaction equation

HRID 446251 reaction equation
[CH3:1][N:2]([CH3:22])[C@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([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)[CH2:4]1>CO.[Pd]>[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:5]1[CH2:6][CH2:7][CH2:8][C@H:3]([N:2]([CH3:22])[CH3:1])[CH2:4]1

Participants

4

Reactant 1

HCID 16109033(S)-N,N-dimethyl-1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-amine

Product 1

HCID 16109028(S)-1-(2-amino-4-(trifluoromethyl)phenyl)-N,N-dimethylpiperidin-3-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)—N,N-Dimethyl-1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-amine (0.82 g, 2.6 mmol) was reduced with Pd/C (10%, 0.27 g) in 10 ml methanol. After approximately 12 h, the reaction was flushed with nitrogen and filtered through a pad of celite, rinsing with methanol. Removal of the solvent in vacuo gave the title compound as an orange-red oil. MS (m/z): 288.2 (M+H)+. Calc'd for C14H20F3N3: 287.32.

Workup

  1. customthe reaction was flushed with nitrogen
  2. filtrationfiltered through a pad of celite
  3. washrinsing with methanol
  4. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-987667eb5ff243e39f9bdb2b753509aa
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Linked notes

Loading…