Potassium Iodide → HCID 58930607, compound

HRID 416220Notes

Reaction equation

HRID 416220 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.Cl.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 135947948HCID 135947948, compound

Product 1

HCID 58930607HCID 58930607, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 18 (1.8 g, 8.71 mmol) in acetone (80 mL) were added 4-(2-chloroethyl)morpholine hydrochloride (1.95 g, 10.5 mmol), potassium iodide (360 mg, 2.2 mmol) and potassium carbonate (6.0 g, 44.0 mmol), respectively. The reaction mixture was refluxed for 16 h and concentrated. The residue was diluted with water and the aqueous phase was extracted twice with EtOAc. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated to form a residue was purified by flash chromatography on silica gel (EtOAc/CH2Cl2, 50/50 to MeOH/CH2Cl2: 2/98) to afford the title compound 19 (2.7 g, 8.4 mmol, 96% yield).

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. concentrationconcentrated
  3. additionThe residue was diluted with water
  4. extractionthe aqueous phase was extracted twice with EtOAc
  5. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto form a residue
  9. customwas purified by flash chromatography on silica gel (EtOAc/CH2Cl2, 50/50 to MeOH/CH2Cl2: 2/98)

Sources & evidence

ORD record
ord-15b5f2df7124488fb3388ab4799570c1
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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