Carbon Dioxide → HCID 12460613, compound

HRID 1646442Notes

Reaction equation

HRID 1646442 reaction equation
[CH2:1]([N:3]([CH2:15][CH3:16])[C:4](=[O:14])[C:5]1[CH:13]=[CH:12][C:11]2[O:10][CH2:9][O:8][C:7]=2[CH:6]=1)[CH3:2].C([Li])(CC)C.[C:22](=[O:24])=[O:23].S(=O)(=O)(O)O>O1CCCC1.O>[CH2:15]([N:3]([CH2:1][CH3:2])[C:4](=[O:14])[C:5]1[C:6](=[C:7]2[O:8][CH2:9][O:10][C:11]2=[CH:12][CH:13]=1)[C:22]([OH:24])=[O:23])[CH3:16]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 1118Sulfuric AcidHCID 27480N,N-Diethyl-3,4-methylenedioxybenzamideHCID 178418400CID 53628100

Product 1

HCID 12460613HCID 12460613, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of N,N-diethylpiperonylamide 10.0 g, 45.0 mmol) in tetrahydrofuran is added dropwise at -65° C. to -55° C. to a mixture of sec-Butyllithium (500 mL, 50.0 mmol, 1M in cyclohexane) in tetrahydrofuran under a nitrogen atmosphere. The reaction mixture is poured over tetrahydrofuran saturated with dry ice, allowed to warm to 0° C., treated slowly with water and acidified to pH 3 with concentrated sulfuric acid. The tetrahydrofuran is removed in vacuo and the aqueous residue is extracted with ethyl acetate. The organic extract is dried (MgSO4) and concentrated in vacuo to a yellow-orange gum, NMR and mass spectrographic analysis show it to be a mixture of starting material and the title product. The above aqueous layer is acidified further to pH 2, extracted with ethyl acetate, and the organic extract is dried (MgSO4) and concentrated in vacuo to yield the title product as a yellow foam, 4.00 g (33.6%) identified by NMR spectral analysis.

Workup

  1. customThe tetrahydrofuran is removed in vacuo
  2. extractionthe aqueous residue is extracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialis dried (MgSO4)
  5. concentrationconcentrated in vacuo to a yellow-orange gum, NMR and mass spectrographic analysis show it
  6. additiona mixture of starting material
  7. extractionextracted with ethyl acetate
  8. extractionthe organic extract
  9. dry with materialis dried (MgSO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-691614bebf9044b1bc187c503af28ee4
Source dataset
uspto-grants-1993_01
Patent number
US05180419

Reaction notes

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