HCID 67520715, compound → HCID 16790869, compound

HRID 1925396Notes

Reaction equation

HRID 1925396 reaction equation
[CH3:1][N:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1[N+:20]([O-])=O)[CH:3]1[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1>CO.[Pd]>[CH3:1][N:2]([CH:3]1[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1)[C:10]1[C:11]([NH2:20])=[CH:12][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 67520715HCID 67520715, compound

Product 1

HCID 16790869HCID 16790869, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N,1-dimethyl-N-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-4-amine (11.3 g, 35.6 mmol) in MeOH (260 mL) at RT was added 10% Pd/C (1.89 g). H2 gas was bubbled through the solution for 5 minutes and the reaction was stirred under an atmosphere of H2 gas. The reaction was monitored by LCMS, and H2 gas was added periodically until consumption of starting material. The mixture was filtered through Celite® with MeOH and concentrated to afford the desired product.

Workup

  1. customH2 gas was bubbled through the solution for 5 minutes
  2. additionwas added periodically until consumption of starting material
  3. filtrationThe mixture was filtered through Celite® with MeOH
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-94c4f751d5c3473790188557a43ba9ed
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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