Hydrazine → 4-(1-Isopropylpiperidin-4-yl)aniline

HRID 1783985Notes

Reaction equation

HRID 1783985 reaction equation
NN.[CH:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)([CH3:5])[CH3:4]>CCO.[Pd]>[CH:3]([N:6]1[CH2:7][CH2:8][CH:9]([C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)[CH2:10][CH2:11]1)([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 574241751-Isopropyl-4-(4-nitrophenyl)piperidine

Product 1

HCID 575900714-(1-Isopropylpiperidin-4-yl)anilineYield 72.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Hydrazine (35% by weight in water, 0.67 mL, 7.2 mmol) and 10% Pd/C (38 mg, 0.03 mmol) are added to a solution of 1-isopropyl-4-(4-nitrophenyl)piperidine (180 mg, 0.72 mmol) in EtOH (10 mL) and the mixture is heated at reflux for 3 h. After cooling, the mixture is filtered through celite and the solvent evaporated. The residue is redissolved in DCM (25 mL), dried over MgSO4 and the solvent evaporated to afford the desired compound as a pale yellow solid (113 mg, 0.52 mmol) which was used without further purification.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 3 h
  3. temperatureAfter cooling
  4. filtrationthe mixture is filtered through celite
  5. customthe solvent evaporated
  6. dissolutionThe residue is redissolved in DCM (25 mL)
  7. dry with materialdried over MgSO4
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-47beca92f7bf46d2831f9c086d6c8527
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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