Diethylcarbamoyl chloride → n,n-Diethyl-(3-morpholin-4-yl-phenoxy)carboxamide

HRID 349698

Reaction equation

HRID 349698 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[CH2:20]([N:22]([CH2:26][CH3:27])[C:23](Cl)=[O:24])[CH3:21]>C(#N)C.CCOC(C)=O>[CH2:20]([N:22]([CH2:26][CH3:27])[C:23]([O:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)[CH:8]=1)=[O:24])[CH3:21]

Participants

6

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 11430Potassium CarbonateHCID 1413433-Morpholinophenol

Product 1

HCID 9878759n,n-Diethyl-(3-morpholin-4-yl-phenoxy)carboxamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of 3-morpholinylphenol (0.34 g; 1.9 mmol) and powdered K2CO3 (0.576 g; 4.2 mmol) in dry acetonitrile (10 mL) was added diethyl carbamylchloride (0.26 mL; 2.0 mmol) via syringe at room temperature under nitrogen atmosphere. The resulting mixture was heated to reflux for 24 hours, then allowed to cool to room temperature. The reaction was diluted with EtOAc (60 mL), washed with water (2×20 mL) and brine, then dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified via radial chromatography (4 mm chromatotron plate with 2:1 hexanes/EtOAc) to provide the carbamate as a clear, colorless oil (0.39 g; 74%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 24 hours
  3. washwashed with water (2×20 mL) and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via radial chromatography (4 mm chromatotron plate with 2:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-b76ca35572524a9080b7fb265fe43dee
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Linked notes

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