Tetrahydrofuran → 4-Dipropylaminomethyl-aniline

HRID 2080755Notes

Reaction equation

HRID 2080755 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.C1COCC1.O.NN>CO.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 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 15871689(4-Nitrobenzyl)dipropylamine

Product 1

HCID 167770114-Dipropylaminomethyl-anilineYield 38%

Reagents, catalysts & solvents 2

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

The compound (2.61 g) obtained in Example 15-1 was dissolved in methanol (25 ml). The solution was added with THF (13 ml), activated carbon (261 mg), and iron trichloride hexahydrate (26.1 mg) and the whole was refluxed for 30 minutes. After having been cooled to room temperature, the solution was added with hydrazine monohydrate (1.88 ml) and then the whole was refluxed for 3 hours. After completion of the reaction, the resultant was subjected to filtration through Celite. The filtrate was subjected to extraction with chloroform and washed with distilled water and a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (865 mg) as a yellow oily substance.

Workup

  1. temperaturethe whole was refluxed for 30 minutes
  2. temperaturethe whole was refluxed for 3 hours
  3. customAfter completion of the reaction
  4. filtrationthe resultant was subjected to filtration through Celite
  5. extractionThe filtrate was subjected to extraction with chloroform
  6. washwashed with distilled water
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. distillationthe solvent was distilled off
  9. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-808775f483a94eb89c7c0c56e380c51b
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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