Propanal → N,N-Bis(2-methylpropyl)prop-1-en-1-amine

HRID 2218554Notes

Reaction equation

HRID 2218554 reaction equation
S([O-])([O-])(=O)=O.[Mg+2].[CH:7](=O)[CH2:8][CH3:9].O.S(=O)(=O)(O)O.[CH2:17]([NH:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH:18]([CH3:20])[CH3:19]>>[CH3:19][CH:18]([CH3:20])[CH2:17][N:21]([CH:7]=[CH:8][CH3:9])[CH2:22][CH:23]([CH3:25])[CH3:24]

Participants

6

Reactant 5

HCID 527PropanalHCID 962WaterHCID 1118Sulfuric AcidHCID 8085DiisobutylamineHCID 24083Sulfuric acid magnesium salt (1:1)2×

Product 1

HCID 54063094N,N-Bis(2-methylpropyl)prop-1-en-1-amineYield 78.8%

Conditions

Temperature
12.5 °C

Procedure

To a suspension of magnesium sulfate (15.1 g) in diisobutylamine (107.3 g) was added dropwise propionaldehyde (24.8 g) at 0-10° C. under a nitrogen atmosphere, and it was stirred at 10-15° C. for 1.5 hours. After ice-cooling, water (90 ml) was added and it was stirred to dissolve the magnesium sulfate. After the removal of the aqueous layer, to the organic layer obtained was added an 8% (w/v) aqueous sulfuric acid solution (300 ml) at 0-5° C. and then stirred for 10 minutes. The aqueous layer was, then, removed again, a 0.5% (w/v) aqueous sodium hydroxide solution (90 ml) was added to the organic layer at 0-5° C., and stirred for 10 minutes. After stirring, the aqueous layer was removed to afford the title compound (57.0 g, yield: 76%, purity: 96.7%) as a colorless oil.

Workup

  1. temperatureAfter ice-cooling
  2. stirringit was stirred
  3. customAfter the removal of the aqueous layer
  4. customto the organic layer obtained
  5. stirringstirred for 10 minutes
  6. customremoved again
  7. additiona 0.5% (w/v) aqueous sodium hydroxide solution (90 ml) was added to the organic layer at 0-5° C.
  8. stirringstirred for 10 minutes
  9. stirringAfter stirring
  10. customthe aqueous layer was removed

Sources & evidence

ORD record
ord-f35d76da0f1644a681883b0fc8c89fcd
Source dataset
uspto-grants-2008_08
Patent number
US07411095B2

Reaction notes

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