Hydrazine hydrate (1:1) → 4-Dipropylaminomethyl-aniline

HRID 348599Notes

Reaction equation

HRID 348599 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][N:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][CH3:12])=[CH:6][CH:5]=1)([O-])=O.O.NN>CO.C1COCC1.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[CH2:10]([N:9]([CH2:8][C:7]1[CH:16]=[CH:17][C:4]([NH2:1])=[CH:5][CH:6]=1)[CH2:13][CH2:14][CH3:15])[CH2:11][CH3:12]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 15871689(4-Nitrobenzyl)dipropylamine

Product 1

HCID 167770114-Dipropylaminomethyl-anilineYield 101.7%

Reagents, catalysts & solvents 3

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound (492 mg) obtained in Example 19-1 was dissolved in methanol (5.0 ml) and THF (2.5 ml). Then, the solution was added with activated carbon (49.0 mg) and iron trichloride hexahydrate (manufactured by Kanto Kagaku) (4.90 mg), followed by refluxing under heating for 30 minutes. After the solution was cooled to room temperature, hydrazine monohydrate (0.35 ml) was added to the solution and then the whole was refluxed for 3 hours under heat. After completion of the reaction, the reaction product was filtrated through Celite and the solvent was then distilled off. After the addition of water, chloroform extraction was performed. The extract was dried with anhydrous magnesium sulfate. The solvent was distilled off, thereby obtaining the subject compound (437 mg) as a yellow oily substance.

Workup

  1. temperatureby refluxing
  2. temperatureunder heating for 30 minutes
  3. temperaturethe whole was refluxed for 3 hours
  4. temperatureunder heat
  5. customAfter completion of the reaction
  6. filtrationthe reaction product was filtrated through Celite
  7. distillationthe solvent was then distilled off
  8. additionAfter the addition of water, chloroform extraction
  9. dry with materialThe extract was dried with anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-df60c42c1e7a4f3aba46d1f30d2a337b
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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