Ethyl Acetate → HCID 69299662, compound

HRID 131262Notes

Reaction equation

HRID 131262 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][NH2:17].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CS(C)=O.O>[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][NH:17][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 66053N,N-DimethylethylenediamineHCID 67976Benzoic acid, 4-fluoro-, ethyl ester

Product 1

HCID 69299662HCID 69299662, compoundYield 44.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 4-fluorobenzoate (20 g), N,N-dimethylethylenediamine (20 g) and potassium carbonate (32.9 g) in dimethylsulfoxide (200 mL) is stirred at 80° C. for 3 days. After cooling to room temperature, to the reaction mixture is added ethyl acetate and water, and the mixture is stirred and extracted with ethyl acetate (×2). The organic layer is treated with 10% HCl to transfer basic materials to the aqueous layer. The aqueous layer is washed with ethyl acetate, neutralized with 10% sodium hydroxide solution and extracted with ethyl acetate (×3). The combined extract is dried over anhydrous sodium sulfate and concentrated in vacuo. The resultant crude product is purified by flash column chromatography on NH-silica gel (Solvent; n-hexane:ethyl acetate=8:1→4:1) to give ethyl 4-[[2-(dimethylamino)ethyl]amino]-benzoate (12.45 g, yield; 44%) as an oil. MS (APCI) m/z: 237 [M+H]+

Workup

  1. extractionextracted with ethyl acetate (×2)
  2. additionThe organic layer is treated with 10% HCl
  3. washThe aqueous layer is washed with ethyl acetate
  4. extractionextracted with ethyl acetate (×3)
  5. extractionThe combined extract
  6. dry with materialis dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resultant crude product is purified by flash column chromatography on NH-silica gel (Solvent; n-hexane:ethyl acetate=8:1→4:1)

Sources & evidence

ORD record
ord-294158ebfda448ce9a2732981fae3c24
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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