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

HRID 552388Notes

Reaction equation

HRID 552388 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].O.NN>C(O)C.[Pd]>[CH:1]([N:4]1[CH2:5][CH2:6][CH:7]([C:10]2[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=2)[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 574241751-Isopropyl-4-(4-nitrophenyl)piperidine

Product 1

HCID 575900714-(1-Isopropylpiperidin-4-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-isopropyl-4-(4-nitro-phenyl)-piperidine (2.405 g, 9.698 mmol), prepared according to Example 5, in ethanol (100 mL) under nitrogen is added Pd/C 10% (515.9 mg, 0.485 mmol), followed by dropwise addition of hydrazine hydrate (2.427 g, 48.49 mmol). The mixture is refluxed overnight until completion of the reaction. After filtration through a celite plug, the solvent is removed under reduced pressure to yield the title compound, which is used as such for the next step.

Workup

  1. temperatureThe mixture is refluxed overnight until completion of the reaction
  2. filtrationAfter filtration through a celite plug
  3. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-4462c8c0f8e54e559ca6ff05c803854f
Source dataset
uspto-grants-2011_05
Patent number
US07951818B2

Reaction notes

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