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

HRID 2218555Notes

Reaction equation

HRID 2218555 reaction equation
S([O-])([O-])(=O)=O.[Mg+2].[CH:7](=O)[CH2:8][CH3:9].O.C(O)(=O)C.[CH2:16]([NH:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH:17]([CH3:19])[CH3:18]>>[CH3:18][CH:17]([CH3:19])[CH2:16][N:20]([CH:7]=[CH:8][CH3:9])[CH2:21][CH:22]([CH3:24])[CH3:23]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 527PropanalHCID 962WaterHCID 8085DiisobutylamineHCID 24083Sulfuric acid magnesium salt (1:1)2×

Product 1

HCID 54063094N,N-Bis(2-methylpropyl)prop-1-en-1-amineYield 88.9%

Conditions

Temperature
12.5 °C

Procedure

To a suspension of magnesium sulfate (10.1 g) in diisobutylamine (72.2 g) was added dropwise propionaldehyde (16.4 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 (60 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 a 9% (w/v) aqueous acetic acid solution (200 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 (60 ml) was added to the organic layer at 0-5° C., and stirred for 5 minutes. After stirring, the aqueous layer was removed to afford the title compound (42.5 g, yield: 81%, purity: 95.3%) 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 (60 ml) was added to the organic layer at 0-5° C.
  8. stirringstirred for 5 minutes
  9. stirringAfter stirring
  10. customthe aqueous layer was removed

Sources & evidence

ORD record
ord-ad0590bb635c405f8a59a8a59fc99182
Source dataset
uspto-grants-2008_08
Patent number
US07411095B2

Reaction notes

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