Hydrazine hydrate (1:1) → 3-Dipropylaminomethylaniline

HRID 1173873Notes

Reaction equation

HRID 1173873 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[CH2:7][N:8]([CH2:12][CH2:13][CH3:14])[CH2:9][CH2:10][CH3:11])([O-])=O.O.NN>CO.C1COCC1.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[CH2:9]([N:8]([CH2:7][C:6]1[CH:5]=[C:4]([CH:17]=[CH:16][CH:15]=1)[NH2:1])[CH2:12][CH2:13][CH3:14])[CH2:10][CH3:11]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13022589(3-Nitro-benzyl)dipropylamine

Product 1

HCID 230793273-DipropylaminomethylanilineYield 66.2%

Reagents, catalysts & solvents 3

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound (595 mg) obtained in Example 33-1 was dissolved in methanol (6.0 ml) and THF (3.0 ml). The solution was added with activated carbon (59.0 mg) and iron trichloride hexahydrate (manufactured by Kanto Kagaku) (5.90 mg), followed by thermal reflux for 30 minutes. After having been cooled to room temperature, the mixture was added with hydrazine monohydrate (0.43 ml) and then subjected to thermal reflux for 24 hours. After completion of the reaction, the mixture was subjected to Celite filtration and the solvent was then distilled off. The residue was added with water and then extracted with chloroform. The extract was dried with anhydrous magnesium sulfate and then solvent was distilled off. Subsequently, the residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (343.9 mg) as a yellow oily substance.

Workup

  1. temperatureby thermal reflux for 30 minutes
  2. temperaturethermal reflux for 24 hours
  3. customAfter completion of the reaction
  4. filtrationthe mixture was subjected to Celite filtration
  5. distillationthe solvent was then distilled off
  6. additionThe residue was added with water
  7. extractionextracted with chloroform
  8. dry with materialThe extract was dried with anhydrous magnesium sulfate
  9. distillationsolvent was distilled off
  10. customSubsequently, the residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-6a8812346d3e486a8ac67e5fa2dbe52c
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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