2-Morpholinoethanol → HCID 24957862, compound

HRID 336668Notes

Reaction equation

HRID 336668 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:13][CH3:14])[CH:12]=1)[CH:9]=[N:8][C:7]([C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([OH:22])=[C:17]([CH3:23])[CH:16]=1)=[CH:6]2.O[CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C(N(CC)C(C)C)(C)C.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.C(OCC)(=O)C>[CH3:23][C:17]1[CH:16]=[C:15]([C:7]2[N:8]=[CH:9][C:10]3[C:5]([CH:6]=2)=[CH:4][C:3]([O:2][CH3:1])=[CH:12][C:11]=3[O:13][CH3:14])[CH:20]=[C:19]([CH3:21])[C:18]=1[O:22][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

7

Reactant 4

HCID 611632-MorpholinoethanolHCID 81531DiisopropylethylamineHCID 5462977Diethyl azodicarboxylateHCID 135907847HCID 135907847, compound

Product 1

HCID 24957862HCID 24957862, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(6,8-dimethoxyisoquinolin-3-yl)-2,6-dimethylphenol (0.309 g, 1.0 mol) in anhydrous THF (20 mL), triphenyl phosphene (0.52 g, 2.0 mmol), 4-(2-hydroxyethyl)morpholine (0.262 g, 2.0 mmol) and N,N-diisopropylethylamine (0.387 g, 3.0 mmol) were added. To this stirred solution was added diethylazodicarboxylate (0.348 g, 2.0 mmol). The reaction mixture was stirred at room temperature overnight under nitrogen, then diluted with ethyl acetate (100 mL). The organic layer was washed with water and brine, and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. The crude material was purified by column chromatography to give 3-[3,5-dimethyl-4-(2-morpholin-4-ylethoxy)phenyl]-6,8-dimethoxyisoquinoline (0.54 g) as a white solid.

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. customThe solvent was removed under reduced pressure
  4. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-1da72e9fdcbe41cc8330a347f9ba310f
Source dataset
uspto-grants-2014_11
Patent number
US08889698B2

Reaction notes

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