Acetone → HCID 18995654, compound

HRID 374984Notes

Reaction equation

HRID 374984 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].C1(CN(CC2C=CC=CC=2)[C:17]2[C:26]3[N:27]=[C:28]([CH2:30][CH2:31][CH2:32]Cl)[NH:29][C:25]=3[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=2)C=CC=CC=1.[CH3:41][C:42]([CH3:44])=O>>[C:42]1([CH2:44][N:29]([CH2:25][C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[C:24]3[C:19]=2[N:18]=[CH:17][C:26]2[N:27]=[C:28]4[CH2:30][CH2:31][CH2:32][N:29]4[C:25]3=2)[CH:32]=[CH:31][CH:30]=[CH:28][CH:41]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 178478459HCID 178478459, compound

Product 1

HCID 18995654HCID 18995654, compound

Procedure

Potassium carbonate (10X excess) and sodium iodide (5X excess) were added to a solution of N,N-bis(phenylmethyl)-2-(3-chloropropyl)-1H-imidazo[4,5-c]quinolin-4-amine (0.8 g, 1.8 mmole) in acetone. The reaction was heated at reflux for 2 hours, filtered and then concentrated under vacuum. The residue was partitioned between methylene chloride and water. The methylene chloride layer was separated, dried over magnesium sulfate and then concentrated under vacuum. The residue was purified by column chromatography (silica gel eluting with 10-30% ethyl acetate in hexanes v/v) to provide 0.25 g of N,N-bis(phenylmethyl)-9,10-dihydro-8H-pyrrolo[1',2':1,2]imidazo[4,5-c]quinolin-4-amine.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 hours
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue was partitioned between methylene chloride and water
  6. customThe methylene chloride layer was separated
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by column chromatography (silica gel eluting with 10-30% ethyl acetate in hexanes v/v)

Sources & evidence

ORD record
ord-440e46a72a374db4b9e3c18eb6675f20
Source dataset
uspto-grants-1996_01
Patent number
US05482936

Reaction notes

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