Allylamine → HCID 4257022, compound

HRID 2303600Notes

Reaction equation

HRID 2303600 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[CH2:7]([NH2:10])[CH:8]=[CH2:9]>O1CCCC1>[CH2:7]([NH:10][C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[CH:8]=[CH2:9]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 8855Butyryl chloride

Product 1

HCID 4257022HCID 4257022, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
15 °C

Procedure

Butyroyl chloride (194.7 g, 1.83 mol) in 1 L of tetrahydrofuran was added to a three neck round bottom flask equipped with a thermometer, stir bar, and dropping funnel. The contents of the flask were then cooled to 15° C. in an ice bath while stirring. Allylamine (208.7 g, 3.65 mol) in 50 mL of tetrahydrofuran was then added slowly through the dropping funnel while maintaining stirring. Throughout the addition, the temperature was maintained at 15° C. After addition was complete, stirring continued for an additional 15 minutes, after which the solid allylamine chloride precipitate was filtered off. The filtrate was concentrated under vacuum to yield 236.4 g of N-allyl butyramide as a colorless viscous liquid.

Workup

  1. customequipped with a thermometer
  2. stirringwhile stirring
  3. temperaturewhile maintaining
  4. stirringstirring
  5. additionThroughout the addition
  6. temperaturethe temperature was maintained at 15° C
  7. additionAfter addition
  8. stirringstirring
  9. filtrationafter which the solid allylamine chloride precipitate was filtered off
  10. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-7da4e42bb8944d0e8c999ec256fa3a29
Source dataset
uspto-grants-2002_08
Patent number
US06433026B1

Reaction notes

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