Morpholine → HCID 57447014, compound

HRID 2366595Notes

Reaction equation

HRID 2366595 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][C:21](OCC)=[O:22])[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:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][C:21]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[O:22])[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

5

Reactant 2

HCID 8083MorpholineHCID 57447013HCID 57447013, compound

Product 1

HCID 57447014HCID 57447014, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

Ethyl 4-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butanoate (6.25 g, 18.3 mmol) and morpholine (16.0 g, 184 mmol) were sealed and heated in a high-pressure vessel at 130° C. overnight. An analysis by TLC indicated the reaction was incomplete. Pyridinium p-toluenesulfonate (100 mg) was added, and the reaction was heated for three days at 105° C. and for one day at 125° C. The solution was allowed to cool and then poured into water (100 mL). The resulting solution was extracted with dichloromethane (3×75 mL), and the combined extracts were dried over potassium carbonate, filtered, and concentrated under reduced pressure. The residue was mixed with ethyl acetate (50 mL) and hexane (200 mL) and sonicated. The solvent was decanted away to afford 6.9 g of 2-(ethoxymethyl)-1-(4-morpholin-4-yl-4-oxobutyl)-1H-imidazo[4,5-c]quinoline as an oil.

Workup

  1. temperaturethe reaction was heated for three days at 105° C. and for one day at 125° C
  2. temperatureto cool
  3. extractionThe resulting solution was extracted with dichloromethane (3×75 mL)
  4. dry with materialthe combined extracts were dried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. additionThe residue was mixed with ethyl acetate (50 mL) and hexane (200 mL)
  8. customsonicated
  9. customThe solvent was decanted away

Sources & evidence

ORD record
ord-cd656bfe9a854b84bc3ffeafd56442bf
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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