HCID 68384944, compound → HCID 68385065, compound

HRID 1047576Notes

Reaction equation

HRID 1047576 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([N+:15]([O-])=O)=[C:12]([CH:14]=2)[NH2:13])[CH2:4][CH2:3]1.[H][H]>C(O)C.[Pd]>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:14]=[C:12]([NH2:13])[C:11]([NH2:15])=[CH:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 68384944HCID 68384944, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68385065HCID 68385065, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-(4-Methylpiperidin-1-yl)-2-nitroaniline (200 mg, 0.850 mmol) was added to 10% Pd/C (10 mg) in ethanol (25 mL) and then hydrogen gas (60 psi) was applied for 24 h at room temperature. Upon TLC-based completion of the reaction, the reaction mixture was filtered through Celite, and the solvent was removed in vacuo. Purification by flash chromatography (5% CH3OH/CH2Cl2) afforded the title compound (150 mg) as a brown solid. 1H NMR: (400 MHz, DMSO-d6): δ 6.35 (d, 1H, J=8.4 Hz), 6.19 (d, 1H, J=2.4 Hz), 5.99 (m, 1H), 4.29 (bs, 2H), 3.92 (bs, 2H), 3.26 (m, 2H), 2.39 (m, 2H), 1.61 (m, 2H), 1.36 (m, 1H), 1.20 (m, 2H), 0.89 (d, 3H, J=6.8 Hz); ESI-MS [M+H]+: 206.1.

Workup

  1. customUpon TLC-based completion of the reaction
  2. filtrationthe reaction mixture was filtered through Celite
  3. customthe solvent was removed in vacuo
  4. customPurification by flash chromatography (5% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-4f17baa6aba642b385e969d9565702f3
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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