Triethylamine → HCID 18916102, compound

HRID 1682387Notes

Reaction equation

HRID 1682387 reaction equation
[C:1]1(=[O:7])[NH:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20](Cl)=[O:21]>C1COCC1>[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20]([N:6]1[CH2:5][CH2:4][CH2:3][CH2:2][C:1]1=[O:7])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 126652-PiperidoneHCID 682422-Furancarbonyl chloride

Product 1

HCID 18916102HCID 18916102, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

All glassware is dried thoroughly, and the reaction is kept under an inert atmosphere (argon) at all times. With stirring, 20.0 g (0.18 mol) of 2-furoic acid (Aldrich) and 40.0 mL (0.53 mol) of thionyl chloride (Aldrich, d=1.631 g/mol) are added to 300 mL THF (Aldrich, HPLC grade) in a single-neck round bottom flask equipped with a reflux condenser and magnetic stirrer. The resulting reaction mixture is heated to reflux and stirred for 16 h. After cooling to room temperature, the solvent and excess thionyl chloride are removed by evaporation under reduced pressure to yield 2-furoyl chloride. In a subsequent reaction, 9.2 g (92 mmol) of valerolactam (Aldrich) and 14.1 mL (101 mmol) of triethylamine (Aldrich, d=0.726 g/mol) are added to 150 mL THF (Aldrich, HPLC grade) in a 3-neck round bottom flask equipped with a reflux condenser, addition funnel, and magnetic stirrer. Addition of a solution of 12.0 g (92 mmol) of the 2-furoyl chloride in 150 mL THF proceeds dropwise over a period of 30 min, and the resulting reaction mixture is heated to reflux and stirred for 16 h. Upon cooling to room temperature, the THF is removed by evaporation under reduced pressure. The solid residue is redissolved in methylene chloride, and extracted several times with 5% aqueous hydrochloric and then deionized water. The organic layer is dried over Na2SO4, filtered, concentrated by removal of solvent, and poured into hexane to precipitate the product. The precipitate is collected by suction filtration, rinsed with hexane, and dried under vacuum to yield N-(2-furoyl)valerolactam as a white, crystalline solid.

Workup

  1. customequipped with a reflux condenser, addition funnel, and magnetic stirrer
  2. customthe resulting reaction mixture
  3. temperatureis heated
  4. temperatureto reflux
  5. customthe THF is removed by evaporation under reduced pressure
  6. dissolutionThe solid residue is redissolved in methylene chloride
  7. extractionextracted several times with 5% aqueous hydrochloric
  8. dry with materialThe organic layer is dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated by removal of solvent
  11. additionpoured into hexane
  12. customto precipitate the product
  13. filtrationThe precipitate is collected by suction filtration
  14. washrinsed with hexane
  15. customdried under vacuum

Sources & evidence

ORD record
ord-47ba2abb03e5480f9f75d840902ad479
Source dataset
uspto-grants-1997_06
Patent number
US05635104

Reaction notes

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