Morpholine → HCID 57447046, compound

HRID 2366650Notes

Reaction equation

HRID 2366650 reaction equation
[CH3:1][C:2]1[N:3]([CH2:15][CH2:16][C:17]([O:19]CC)=O)[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:14]=1.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[CH3:1][C:2]1[N:3]([CH2:15][CH2:16][C:17]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[O:19])[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:14]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 57447045HCID 57447045, compound

Product 1

HCID 57447046HCID 57447046, compoundYield 98.7%

Procedure

A solution of ethyl 3-(2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)propanoate (4.0 g, 15 mmol) and morpholine (10 mL, 100 mmol) was heated for three days in a high-pressure vessel at 100° C., allowed to cool to ambient temperature, and concentrated under reduced pressure. The residue was dissolved in dichloromethane, and the resulting solution was washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 4.8 g of 2-methyl-1-(3-morpholin-4-yl-3-oxopropyl)-1H-imidazo[4,5-c]quinoline.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washthe resulting solution was washed with saturated aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-204d1548cb90413996acd53815266924
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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