7-[4-Nitro-3-(trifluoromethyl)phenyl]-7-azabicyclo[2.2.1]heptane → 4-(7-Azabicyclo[2.2.1]heptan-7-yl)-2-(trifluoromethyl)aniline

HRID 335393Notes

Reaction equation

HRID 335393 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]3[CH2:15][CH2:16][CH:11]2[CH2:12][CH2:13]3)=[CH:6][C:5]=1[C:17]([F:20])([F:19])[F:18])([O-])=O>[Pd]>[CH:11]12[N:10]([C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[C:5]([C:17]([F:20])([F:18])[F:19])[CH:6]=3)[CH:14]([CH2:13][CH2:12]1)[CH2:15][CH2:16]2

Participants

3

Reactant 1

HCID 575168437-[4-Nitro-3-(trifluoromethyl)phenyl]-7-azabicyclo[2.2.1]heptane

Product 1

HCID 529133904-(7-Azabicyclo[2.2.1]heptan-7-yl)-2-(trifluoromethyl)anilineYield 91%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A flask charged with 7-[4-nitro-3-(trifluoromethyl)phenyl]-7-azabicyclo[2.2.1]heptane (26) (7.07 g, 24.70 mmol) and 10% Pd/C (0.71 g, 6.64 mmol) was evacuated and then flushed with nitrogen. Ethanol (22 ml) was added and the reaction flask was fitted with a hydrogen balloon. After stirring vigorously for 12 h, the reaction mixture was purged with nitrogen and Pd/C was removed by filtration. The filtrate was concentrated to a dark oil under reduced pressure and the residue purified by silica gel chromatography (0-15% ethyl acetate in hexanes) to provide 447-azabicyclo[2.2.1]heptan-7-yl)-2-(trifluoromethyl)aniline (3) as a purple solid (5.76 g, 91% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 6.95 (dd, J=2.3, 8.8 Hz, 1H), 6.79 (d, J=2.6 Hz, 1H), 6.72 (d, J=8.8 Hz, 1H), 4.89 (s, 2H), 4.09 (s, 2H), 1.61-1.59 (m, 4H) and 1.35 (d, J=6.8 Hz, 4H).

Workup

  1. customwas evacuated
  2. customflushed with nitrogen
  3. additionEthanol (22 ml) was added
  4. customthe reaction flask was fitted with a hydrogen balloon
  5. customthe reaction mixture was purged with nitrogen and Pd/C
  6. customwas removed by filtration
  7. concentrationThe filtrate was concentrated to a dark oil under reduced pressure
  8. customthe residue purified by silica gel chromatography (0-15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0ed9ec78e283479eb7ea973d923b54fa
Source dataset
uspto-grants-2014_11
Patent number
US08884018B2

Reaction notes

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