Dimethylformamide → 1-[3,5-Dimethoxy-4-(2-morpholin-4-yl-ethoxy)-phenyl)ethanone

HRID 497032

Reaction equation

HRID 497032 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12](=[O:14])[CH3:13])[CH:6]=[C:7]([O:10][CH3:11])[C:8]=1[OH:9].Cl.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:11][O:10][C:7]1[CH:6]=[C:5]([C:12](=[O:14])[CH3:13])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 17198AcetosyringoneHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 223181171-[3,5-Dimethoxy-4-(2-morpholin-4-yl-ethoxy)-phenyl)ethanoneYield 69.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

In a vial, 500 mg (2.5 mmol) of 3′,5′-dimethoxy-4′-hydroxyacetophenone was combined with 4-(2-chloroethyl)morpholine hydrochloride (600 mg, 3.2 mmol), and powdered potassium carbonate (1.5 g, excess). Dimethylformamide (2 mL) was added, the vial was sealed, and the rxn was heated to 80° C. overnight. The reaction was diluted with water and extracted with diethyl ether. The organic extract was washed with brine, dried (Na2SO4), and evaporated in vacuo to afford 540 mg (67%) of 14 as a white solid.

Workup

  1. customthe vial was sealed
  2. extractionextracted with diethyl ether
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-25d2e860e6bc4b9cb622bc039d6f7343
Source dataset
uspto-grants-2005_09
Patent number
US06949544B2

Linked notes

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