Butanal → N,N-Di(propan-2-yl)but-1-en-1-amine

HRID 1415784Notes

Reaction equation

HRID 1415784 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH3:4].[CH:6]([NH:9][CH:10]([CH3:12])[CH3:11])([CH3:8])[CH3:7]>C1C=CC=CC=1>[CH:6]([N:9]([CH:1]=[CH:2][CH2:3][CH3:4])[CH:10]([CH3:12])[CH3:11])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 261ButanalHCID 7912Diisopropylamine

Product 1

HCID 53723651N,N-Di(propan-2-yl)but-1-en-1-amineYield 65%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

6.25 ml (69.3 mmol) of butyraldehyde and 19.44 ml (139 mmol) of diisopropylamine were dissolved in 30 ml of benzene, and the mixture was heated under reflux, while removing the water produced, until the production of water stopped (about 15 hours). The solvent was then removed by distillation under reduced pressure, and the residue was distilled under atmospheric pressure. Those fractions of the distillate having a boiling point of from 140 to 160° C. were collected, to give 6.95 g of the title compound as a pale yellow oily substance (yield 65%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customwhile removing the water
  4. customproduced, until the production of water
  5. custom(about 15 hours)
  6. customThe solvent was then removed by distillation under reduced pressure
  7. distillationthe residue was distilled under atmospheric pressure
  8. customof from 140 to 160° C.
  9. customwere collected

Sources & evidence

ORD record
ord-6b344b900a96485781fcc3d6e5b58b84
Source dataset
uspto-grants-1999_06
Patent number
US05908858

Reaction notes

Loading…