Potassium Iodide → HCID 58424875, compound

HRID 2409415Notes

Reaction equation

HRID 2409415 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]([CH2:15][O:16][CH3:17])[C:7](=[O:14])[C:8]3[CH:9]=[CH:10][CH:11]=[N:12][C:13]=3[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl.[CH3:29][N:30]([CH2:32][CH2:33]Cl)[CH3:31]>CN(C)C=O>[CH3:29][N:30]([CH3:31])[CH2:32][CH2:33][O:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]([CH2:15][O:16][CH3:17])[C:7](=[O:14])[C:8]3[CH:9]=[CH:10][CH:11]=[N:12][C:13]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 58424899HCID 58424899, compound

Product 1

HCID 58424875HCID 58424875, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (60 mg, 0.234 mmol) prepared in step 5 was dissolved in N,N-dimethylformamide (5 ml), added with potassium carbonate (161 mg, 1.17 mmol) and potassium iodide (8 mg, 0.047 mmol). After stirring for 30 minutes, N,N-dimethylaminoethyl chloride hydrochloride was added at room temperature and the resulting mixture was stirred for one more day at 70° C. The mixture was extracted chloroform, dried over anhydrous magnesium sulfate, concentrated to dryness. The residue was then purified by flash column chromatography (chloroform:methanol=10:1) to obtain the title compound (40 mg, yield: 53%, white solid).

Workup

  1. stirringthe resulting mixture was stirred for one more day at 70° C
  2. extractionThe mixture was extracted chloroform
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated to dryness
  5. customThe residue was then purified by flash column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-3b70b6a549d742c5b3de70836a8c6606
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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