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

HRID 1434516Notes

Reaction equation

HRID 1434516 reaction equation
[F:1][C:2]1[CH:8]=[C:7](I)[CH:6]=[CH:5][C:3]=1[NH2:4].[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][C:11]1=[O:16].C(=O)([O-])[O-].[K+].[K+].CNCCNC>C1(C)C=CC=CC=1.[Cu]I.O>[NH2:4][C:3]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][C:11]2=[O:16])=[CH:8][C:2]=1[F:1]

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 669533-MorpholinoneHCID 1856942-Fluoro-4-iodoaniline

Product 1

HCID 534177984-(4-Amino-3-fluorophenyl)morpholin-3-one

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

2.0 g (8.4 mmol) 2-fluoro-4-iodo-aniline, 860 mg (8.5 mmol) morpholin-3-one, 162 mg (0.86 mmol) copper(I)iodide, 2.33 g (16.86 mmol) potassium carbonate and 91 μl N,N′-dimethylethylenediamine are suspended in 18 ml of toluene under an argon atmosphere and stirred for two hours in a microwave at a power of 35 Watts at 140° C. Water is added and the mixture is extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulphate and evaporated to dryness. The residue is purified by chromatography on silica gel (eluant: dichloromethane/methanol 50:1).

Workup

  1. extractionthe mixture is extracted three times with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. customevaporated to dryness
  4. customThe residue is purified by chromatography on silica gel (eluant: dichloromethane/methanol 50:1)

Sources & evidence

ORD record
ord-f8d38b09f7904b99ac4181ecc9c58354
Source dataset
uspto-grants-2009_11
Patent number
US07615549B2

Reaction notes

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