Triethylamine → HCID 18401839, compound

HRID 1182623Notes

Reaction equation

HRID 1182623 reaction equation
[CH:1]1C2C=CC3C=CC=CC=3C(C(O)C)C=2C=CC=1.C([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])C.[CH2:26]=[C:27]1[O:31][C:29](=[O:30])[CH2:28]1.[C:32](=[O:35])([O-])[OH:33].[Na+].[Cl:37][C:38]1[CH:39]=C([CH:43]=[CH:44][CH:45]=1)C=O>C1(C)C=CC=CC=1.CC(O)C>[Cl:37][C:38]1[CH:39]=[C:26]([CH:27]2[C:1]([C:32]([OH:33])=[O:35])=[C:22]([CH3:23])[NH:21][C:24]([CH3:25])=[C:28]2[C:29]([OH:31])=[O:30])[CH:43]=[CH:44][CH:45]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 114773-ChlorobenzaldehydeHCID 12661DiketeneHCID 516892Sodium BicarbonateHCID 69074895HCID 69074895, compound

Product 1

HCID 18401839HCID 18401839, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

472 mg (2.0 mmol) of 1-(5H-dibenzo[a,d] cyclohepten-5-yl) ethanol, 0.03 ml (0.2 mmol) of triethylamine and 0.345 ml (4.47 mmol) of diketene were heated and stirred in 10 ml of toluene at 80° C. for 3.5 hours. After saturated aqueous sodium hydrogencarbonate solution was added at room temperature, the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. 20 ml of 2-propanol, 312 mg (2.02 mmol) of 3-aminocrotonate 2-cyanoethyl and 0.23 ml (2.03 mmol) of 3-chlorobenzaldehyde were added to the residue and the residue was heated and stirred at 80° C. overnight. After evaporating 2-propanol under reduced pressure, saturated aqueous sodium chloride solution was added and the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the basic silica gel chromatography (hexane/ethyl acetate=9/1 to 1/3) to obtain the title compound.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. temperaturethe residue was heated
  5. customAfter evaporating 2-propanol under reduced pressure, saturated aqueous sodium chloride solution
  6. additionwas added
  7. extractionthe reaction mixture was extracted with ethyl acetate
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by the basic silica gel chromatography (hexane/ethyl acetate=9/1 to 1/3)

Sources & evidence

ORD record
ord-00c4a2a9d9c6479cbb78d7b2f443665f
Source dataset
uspto-grants-2007_10
Patent number
US07288544B2

Reaction notes

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