N,N'-Dimethylethylenediamine → 4-(4-Aminophenyl)morpholin-3-one

HRID 2244994Notes

Reaction equation

HRID 2244994 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][C:2]1=[O:7].I[C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.CNCCNC.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.[Cu]I>[O:7]=[C:2]1[CH2:3][O:4][CH2:5][CH2:6][N:1]1[C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 108934-IodoanilineHCID 11430Potassium CarbonateHCID 669533-Morpholinone

Product 1

HCID 111948544-(4-Aminophenyl)morpholin-3-oneYield 50.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

To a blue solution of 3-morpholinone (250 mg, 2.48 mmol), 4-iodoaniline (650 mg, 2.97 mmol), CuI (47 mg, 0.25 mmol) and N,N′-dimethylethylenediamine (0.040 mL, 0.372 mmol) in dioxane (5 mL) in a pressure bottle, K2CO3 (683 mg, 4.95 mmol) was added. The mixture was heated at 110 C overnight. After being cooled to room temperature, the crude dark solution was loaded to two preparative TLC plates, eluted with EtOAc/MeOH (95/5) to give the desired product as off-white solid (240 mg). MS 193.1 (M+H).

Workup

  1. temperatureThe mixture was heated at 110 C overnight
  2. washeluted with EtOAc/MeOH (95/5)

Sources & evidence

ORD record
ord-6a71d6606dd34a08b8129424f10fde45
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

Loading…