Morpholine → HCID 69506687, compound

HRID 2366653Notes

Reaction equation

HRID 2366653 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][C:20](OCC)=[O:21])[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:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][C:20]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:21])[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 57447047HCID 57447047, compound

Product 1

HCID 69506687HCID 69506687, compoundYield 92.3%

Conditions

Temperature
110 °C

Procedure

A solution of ethyl 3-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)propanoate (5.0 g, 15 mmol) and morpholine (10 mL, 100 mmol) was heated overnight in a high-pressure vessel at 90° C. An analysis by HPLC indicated the reaction was incomplete. The reaction was then heated overnight in a high-pressure vessel at 110° C., allowed to cool to ambient temperature, and concentrated under reduced pressure to provide 5.1 g of 2-(ethoxymethyl)-1-(3-morpholin-4-yl-3-oxopropyl)-1H-imidazo[4,5-c]quinoline.

Workup

  1. temperatureto cool to ambient temperature
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4914a465d5e8484a9421c6b547cace03
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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