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 400986Notes

Reaction equation

HRID 400986 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)aniline

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A flask charged with 7-[4-nitro-3-(trifluoromethyl)phenyl]-7-azabicyclo[2.2.1]heptane (10A) (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 the Pd/C was removed by filtration. The filtrate was concentrated to a dark oil under reduced pressure which was purified by silica gel chromatography (0-15% ethyl acetate in hexanes) to provide 4-(7-azabicyclo[2.2.1]heptan-7-yl)-2-(trifluoromethyl)aniline (11A) as a purple solid. 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
  6. customthe Pd/C was removed by filtration
  7. concentrationThe filtrate was concentrated to a dark oil under reduced pressure which
  8. customwas purified by silica gel chromatography (0-15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-79f158a85e7248a9b34624038c01af40
Source dataset
uspto-grants-2014_06
Patent number
US08741922B2

Reaction notes

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