Water → 4-[4-(3-Dimethylamino-benzoylamino)-phenyl]-butyric acid ethyl ester

HRID 1023700

Reaction equation

HRID 1023700 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[CH2:13]([O:15][C:16](=[O:27])[CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1)[CH3:14].C(N(CC)CC)C.O>C1COCC1>[CH2:13]([O:15][C:16](=[O:27])[CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([NH:26][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([N:2]([CH3:12])[CH3:1])[CH:4]=2)=[CH:24][CH:25]=1)[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 70103423-Dimethylaminobenzoyl chlorideHCID 10013251Ethyl 4-(4-aminophenyl)butanoate

Product 1

HCID 670453314-[4-(3-Dimethylamino-benzoylamino)-phenyl]-butyric acid ethyl esterYield 97.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-dimethylaminobenzoyl chloride (0.19 g, 1.01 mmol) in THF (6 ml) was added dropwise to a solution of 4-(4-aminophenyl)butyric acid ethyl ester (0.26 g, 1.24 mmol) and triethylamine (0.31 g, 3.11 mmol) in THF (8 ml) under ice cooling. The reaction solution was stirred at room temperature for 8 hours, then added with water, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous ammonium chloride and saturated brine, then dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=15:1) to obtain 4-[4-(3-dimethylamino-benzoylamino)-phenyl]-butyric acid ethyl ester as a brown oily substance (0.36 g, yield: 97.5%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous ammonium chloride and saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-537ee15699e143968a5b63286d5a401a
Source dataset
uspto-grants-2014_05
Patent number
US08722723B2

Linked notes

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