Sodium hydride → N,N-dibenzyl-1-(4-chlorobutyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 432842Notes

Reaction equation

HRID 432842 reaction equation
[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:9]1[C:18]2[N:19]=[CH:20][NH:21][C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Cl:31][CH2:32][CH2:33][CH2:34][CH2:35]I>CN(C)C=O>[CH2:22]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[C:18]2[N:19]=[CH:20][N:21]([CH2:35][CH2:34][CH2:33][CH2:32][Cl:31])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 825271-Chloro-4-iodobutaneHCID 178420342HCID 178420342, compound

Product 1

HCID 22320444N,N-dibenzyl-1-(4-chlorobutyl)-1H-imidazo[4,5-c]quinolin-4-amineYield 82.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A round bottom flask was charged with a magnetic stir bar, N,N-dibenzyl-1H-imidazo[4,5-c]quinolin-4-amine (20.0 g, 55.04 mmol), sodium hydride (3.3 g, 60% dispersion, 82.56 mmol), and anhydrous dimethyl formamide (275 mL) under a nitrogen atmosphere. After the reaction mixture had stirred at ambient temperature for 2 hours, 4-chloro-1-iodobutane (19.23 g, 88.06 mmol) was added and the resulting homogeneous solution was stirred at ambient temperature for 48 hours at which time the starting material was consumed. The solution was partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to afford a light yellow solid. The material was recrystallized from ethyl acetate and hexanes to give N,N-dibenzyl-1-(4-chlorobutyl)-1H-imidazo[4,5-c]quinolin-4-amine (20.7 g, 45.49 mmol) as white needles. MS (CI) for C28H27ClN4 m/z 455 (MH+), 365, 329, 239

Workup

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. stirringthe resulting homogeneous solution was stirred at ambient temperature for 48 hours at which time the starting material
  3. customwas consumed
  4. customThe solution was partitioned between ethyl acetate and water
  5. customThe layers were separated
  6. washthe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto afford a light yellow solid
  11. customThe material was recrystallized from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-ca6fdfa8e3674158b51a03d1cc07a845
Source dataset
uspto-grants-2003_12
Patent number
US06664264B2

Reaction notes

Loading…