Allylamine → HCID 4257022, compound

HRID 1976186Notes

Reaction equation

HRID 1976186 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 8028TetrahydrofuranSolvent

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 tetahydrofuran 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-8838492858b140c09c7328c40267f41a
Source dataset
uspto-grants-2001_05
Patent number
US06225355B1

Reaction notes

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