Allylamine → HCID 4153372, compound

HRID 1837780Notes

Reaction equation

HRID 1837780 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:9]([NH2:12])[CH:10]=[CH2:11]>O1CCCC1>[CH2:9]([NH:12][C:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:10]=[CH2:11]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 67340Hexanoyl chloride

Product 1

HCID 4153372HCID 4153372, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
15 °C

Procedure

Hexanoyl chloride (33 g, 0.25 mol) in 250 mL 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 (28.6 g, 0.5 mol) in 200 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 filtration was concentrated under vacuum to yield 37 g of N-allyl hexanamide 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. filtrationThe filtration
  11. concentrationwas concentrated under vacuum

Sources & evidence

ORD record
ord-9cd4ade9c5ee422ab0b9dcda02142942
Source dataset
uspto-grants-2004_08
Patent number
US06784254B2

Reaction notes

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