Isobutyraldehyde → n-benzyl-2-methylpropan-1-amine

HRID 325756Notes

Reaction equation

HRID 325756 reaction equation
[CH:1](=O)[CH:2]([CH3:4])[CH3:3].[CH2:6]([NH2:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.P(O)(O)O>O>[CH2:6]([NH:13][CH2:1][CH:2]([CH3:4])[CH3:3])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6561IsobutyraldehydeHCID 7504BenzylamineHCID 107909Phosphorous acid

Product 1

HCID 211729n-benzyl-2-methylpropan-1-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the imine from isobutyraldehyde and benzylamine (48.4 g; 0.3 mole) was added phosphorous acid (24.6 g; 0.3 mole) and the mixture slowly warmed while stirring. As the internal temperature reached 70°-75° a vigorous exothermic reaction ensued taking the temperature to 130°-135°. After maintaining at 130°-140° for 30 mins. the viscous product was cooled to 100° and diluted with water. Basification and extraction with chloroform gave crude amine after solvent evaporation. Distillation gave pure N-benzylisobutylamine, 13.6 g (28%) bp 94°-99°/5.6 mm. Nmr confirmed the assigned structure.

Workup

  1. temperaturethe mixture slowly warmed
  2. customreached 70°-75°
  3. customa vigorous exothermic reaction
  4. customto 130°-135°
  5. temperatureAfter maintaining at 130°-140° for 30 mins
  6. temperaturethe viscous product was cooled to 100°
  7. extractionBasification and extraction with chloroform
  8. customgave crude amine
  9. customafter solvent evaporation
  10. distillationDistillation

Sources & evidence

ORD record
ord-b62e64ae25184cb0b39b044cb3a90ccc
Source dataset
uspto-grants-1984_04
Patent number
US04442286

Reaction notes

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