Allylamine → HCID 54558578, compound

HRID 2226355Notes

Reaction equation

HRID 2226355 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[F:5][C:6]([F:35])([C:31]([F:34])([F:33])[F:32])[C:7]([F:30])([F:29])[C:8]([F:28])([F:27])[C:9]([F:26])([F:25])[C:10]([F:24])([F:23])[C:11]([F:22])([F:21])[C:12]([F:20])([F:19])[C:13]([F:18])([F:17])[C:14](Cl)=[O:15]>C(OC(C)C)(C)C>[CH2:1]([NH:4][C:14](=[O:15])[C:13]([F:17])([F:18])[C:12]([F:19])([F:20])[C:11]([F:21])([F:22])[C:10]([F:23])([F:24])[C:9]([F:25])([F:26])[C:8]([F:28])([F:27])[C:7]([F:30])([F:29])[C:6]([F:35])([F:5])[C:31]([F:34])([F:33])[F:32])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 13196894Nonadecafluorodecanoyl chloride

Product 1

HCID 54558578HCID 54558578, compound

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent3×

Conditions

Temperature
30 °C

Procedure

Allyl amine (6.03 milliliters, 3.0 molar equivalent) and isopropyl ether (35.0 milliliters) were added to a 3-neck 100-milliliter round bottom flask equipped with water cooled condenser (to a nitrogen inlet), dropping funnel and thermometer adapter (to a Thermowatch device) at room temperature under a nitrogen blanket. A solution of nonadecafluoro-1-decanoyl chloride (14.27 grams, 1.0 molar equivalent) in 5.0 milliliters isopropyl ether was added by the dropping funnel over 2 hours while maintaining the temperature below 30° C. After the addition was completed, the reaction mixture was heated for 2 hours at 30° C., followed by additional treating for 2 hours at 40° C. After cooling the mixture to room temperature, the mixture was diluted with 100 milliliters isopropyl ether and washed with 9% aqueous hydrochloric acid solution (75 milliliters). The aqueous layer was extracted with 50 milliliters isopropyl ether. The combined organic layers were evaporated in vacuo to give a red solid. High vacuum distillation produced 13.03 grams (88% isolated yield) of a light yellow solid (boiling point 100° C., 0.1 millimeters Hg).

Workup

  1. customequipped with water cooled condenser (to a nitrogen inlet)
  2. customat room temperature
  3. temperaturewhile maintaining the temperature below 30° C
  4. additionAfter the addition
  5. additionby additional treating for 2 hours at 40° C
  6. temperatureAfter cooling the mixture to room temperature
  7. washwashed with 9% aqueous hydrochloric acid solution (75 milliliters)
  8. extractionThe aqueous layer was extracted with 50 milliliters isopropyl ether
  9. customThe combined organic layers were evaporated in vacuo
  10. customto give a red solid
  11. distillationHigh vacuum distillation
  12. customproduced
  13. custom13.03 grams (88% isolated yield) of a light yellow solid (boiling point 100° C., 0.1 millimeters Hg)

Sources & evidence

ORD record
ord-a498b77062a94026a609a5e8cf2776b1
Source dataset
uspto-grants-1994_09
Patent number
US05348769

Reaction notes

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