Morpholine → HCID 19032367, compound

HRID 266134Notes

Reaction equation

HRID 266134 reaction equation
Cl[CH2:2][C:3]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:10]2[C:5](=[CH:6][C:7]([O:28][CH3:29])=[C:8]([O:26][CH3:27])[CH:9]=2)[N:4]=1.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>CO>[CH3:27][O:26][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[O:28][CH3:29])[N:4]=[C:3]([CH2:2][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]2[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 10669561HCID 10669561, compound

Product 1

HCID 19032367HCID 19032367, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 2-chloromethyl-6,7-dimethoxy-4-(4-methoxyphenyl)quinoline-3-carboxylate (2.0 g), morpholine (2.5 g) and methanol (30 ml) was stirred at room temperature for 17 hours. The reaction mixture was concentrated under reduced pressure, and dichloromethane was added to the residue. The mixture was washed with water and dried over magnesium sulfate, and the solvent was evaporated. The resulting crystals were separated by filtration and recrystallized from ethanol to give ethyl 6,7-dimethoxy-4-(4-methoxyphenyl)-2-morpholinomethylquinoline-3-carboxylate (1.65 g, 74%). Colorless prisms, mp. 165°-166° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and dichloromethane
  2. additionwas added to the residue
  3. washThe mixture was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe resulting crystals were separated by filtration
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-9ba9f53021e646808ba22177b79433ac
Source dataset
uspto-grants-1997_07
Patent number
US05650410

Reaction notes

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