1-(2-Fluoro-4-nitrophenyl)piperidine → 3-Fluoro-4-(piperidin-1-yl)aniline

HRID 1822921Notes

Reaction equation

HRID 1822921 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[NH2:8]

Participants

4

Reactant 1

HCID 107043451-(2-Fluoro-4-nitrophenyl)piperidine

Product 1

HCID 64857583-Fluoro-4-(piperidin-1-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 10A (12.7 mmol) was hydrogenated (balloon) as a solution in ethyl acetate over 5% Pd/C overnight at room temperature. The mixture was filtered through Celite and the filtrate was concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 6.72–6.78 (m, 1H), 6.26–6.34 (m, 2H), 4.92 (br s, 2H), 2.76 (m, 4H), 1.56–1.63 (m, 4H), 1.42–1.49 (m, 2H); MS (APCI+) m/z 195.

Workup

  1. customat room temperature
  2. filtrationThe mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2fff4233045e498aa1b0bfae2f6519df
Source dataset
uspto-grants-2006_05
Patent number
US07037927B2

Reaction notes

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