Diethylamine → Methyl 2-(2-(benzyloxy)-5-(2-(diethylamino)ethoxy)benzamido)-4-phenylbenzoate

HRID 454663Notes

Reaction equation

HRID 454663 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([NH:9][CH2:10][CH3:11])[CH3:8].[CH2:12]([O:19][C:20]1[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH2:47]Br)=[CH:41][C:21]=1[C:22]([NH:24][C:25]1[CH:34]=[C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:32]=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28])=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O.CC(C)=O>[CH2:12]([O:19][C:20]1[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH2:47][N:9]([CH2:10][CH3:11])[CH2:7][CH3:8])=[CH:41][C:21]=1[C:22]([NH:24][C:25]1[CH:34]=[C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:32]=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28])=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 8021Diethylamine4×HCID 11430Potassium Carbonate4×HCID 516892Sodium BicarbonateHCID 66990627Methyl 2-(2-(benzyloxy)-5-(2-bromoethoxy)benzamido)-4-phenylbenzoate

Product 1

HCID 66990476Methyl 2-(2-(benzyloxy)-5-(2-(diethylamino)ethoxy)benzamido)-4-phenylbenzoate

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.15 g) and diethylamine (0.11 mL) were added to an acetone (2.0 mL) solution of methyl 2-(2-(benzyloxy)-5-(2-bromoethoxy)benzamido)-4-phenylbenzoate (0.20 g), followed by heating to reflux for 4 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then potassium carbonate (0.049 g) and diethylamine (0.037 mL) were added thereto, followed by heating to reflux for 1 hour. The reaction mixture was cooled to room temperature, and then potassium carbonate (0.049 g) and diethylamine (0.037 mL) were added thereto, followed by heating to reflux for 1 hour and 15 minutes. The reaction mixture was cooled to room temperature, and then potassium carbonate (0.049 g) and diethylamine (0.037 mL) were added thereto, followed by heating to reflux for 5 hours and 30 minutes. The reaction mixture was cooled to room temperature, and water, a saturated aqueous solution of sodium bicarbonate, and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-97% chloroform/methanol] to obtain 0.15 g of methyl 2-(2-(benzyloxy)-5-(2-(diethylamino)ethoxy)benzamido)-4-phenylbenzoate.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 4 hour and 30 minutes
  3. temperatureby heating
  4. temperatureto reflux for 1 hour
  5. temperatureThe reaction mixture was cooled to room temperature
  6. temperatureby heating
  7. temperatureto reflux for 1 hour and 15 minutes
  8. temperatureThe reaction mixture was cooled to room temperature
  9. temperatureby heating
  10. temperatureto reflux for 5 hours and 30 minutes
  11. temperatureThe reaction mixture was cooled to room temperature
  12. customThe organic layer was separated
  13. washwashed with a saturated aqueous solution of sodium chloride
  14. dry with materialdried over anhydrous magnesium sulfate
  15. customthe solvent was evaporated under reduced pressure
  16. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-97% chloroform/methanol]

Sources & evidence

ORD record
ord-a61e2718493b4f3ab76d92ceb9376ccd
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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