Acetone → HCID 67771632, compound

HRID 374978Notes

Reaction equation

HRID 374978 reaction equation
[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].C1(CN(CC2C=CC=CC=2)[C:17]2[C:26]3[N:27]=[C:28]([CH2:30][CH2:31][CH:32]([CH3:35])[CH2:33]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.[CH3:43][C:44]([CH3:46])=O>>[C:44]1([CH2:46][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][CH:32]([CH3:35])[CH2:33][N:29]4[C:25]3=2)[CH:32]=[CH:31][CH:30]=[CH:28][CH:43]=1

Participants

5

Reactant 4

HCID 180Acetone2×HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 178448406HCID 178448406, compound

Product 1

HCID 67771632HCID 67771632, compound

Procedure

A large excess (about 10 fold) of both sodium iodide and potassium carbonate were added to a solution of N,N-bis(phenylmethyl)-2-(4-chloro-3-methylbutyl)-1H-imidazo[4,5-c]quinolin-4-amine (about 0.5 g) in acetone (about 75 mL). The reaction mixture was heated at reflux overnight, diluted with additional acetone, filtered and then concentrated under vacuum. The residue was washed with methylene chloride to recover the product from salts then purified by column chromatography (silica gel eluting with 3% ethyl acetate in methylene chloride v/v) to provide 0.35 g of N,N-bis(phenylmethyl)-8,9,10,11 tetrahydro-10-methylpyrido[1',2':1,2]imidazo[4,5-c]quinolin-4-amine.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. washThe residue was washed with methylene chloride
  6. customto recover the product from salts
  7. customthen purified by column chromatography (silica gel eluting with 3% ethyl acetate in methylene chloride v/v)

Sources & evidence

ORD record
ord-d9db5732f45f4c5f9e8fc0a4bb245e97
Source dataset
uspto-grants-1996_01
Patent number
US05482936

Reaction notes

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