Morpholine → HCID 69506762, compound

HRID 2366621Notes

Reaction equation

HRID 2366621 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](OCC)=[O:24])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:24])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 57447030HCID 57447030, compound

Product 1

HCID 69506762HCID 69506762, compound

Procedure

A solution of ethyl 6-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanoate (4.0 g, 11 mmol) in morpholine (7 mL) was heated at reflux for three days, allowed to cool to ambient temperature, and concentrated under reduced pressure. The residue was dissolved in dichloromethane; the resulting solution was washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, and concentrated under reduced pressure to provide 4.4 g of 2-(ethoxymethyl)-1-(6-morpholin-4-yl-6-oxohexyl)-1H-imidazo[4,5-c]quinoline.

Workup

  1. temperatureat reflux for three days
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washthe resulting solution was washed sequentially with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-59c3a582f7b3416eb10877e29f62ede1
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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