Potassium Carbonate → 3,5-Dimethoxy-4-(2-morpholin-4-yl ethoxy)benzoic acid methyl ester

HRID 601022Notes

Reaction equation

HRID 601022 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:14][CH3:15])[C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7].Cl.Cl[CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[C:11]([O:14][CH3:15])[C:12]([O:13][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 70164Methyl SyringateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 589768063,5-Dimethoxy-4-(2-morpholin-4-yl ethoxy)benzoic acid methyl esterYield 105.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3,5-dimethoxy-4-hydroxybenzoate (3.0 g, 14 mmol) in DMF (10 mL) was added 4-(2-chloroethyl)-morpholine hydrochloride (3.99 g, 21 mmol) and solid K2CO3 (8.4 g, 60 mmol). The mixture was heated at 60 C under N2 for 30 h. Diluted with EtOAc (100 mL) and washed with H20 (2×50 mL), back extracted the aqueous phase, and washed combined organics with brine. Dried over Na2SO4, filtered and evaporated to give the product as a brown solid (4.79 g, quantitative). 1H-NMR (CDCl3, 500 MHz 7.28 (s, 2H), 4.15 (t, 2H), 3.91 (s, 3H), 3.88 (s, 6H), 3.75-3.71 (m, 4H), 2.78 (t, 2H), 2.59 (br s, 4H) ppm; MS (FIA) 326.17 (M+H)

Workup

  1. temperatureThe mixture was heated at 60 C under N2 for 30 h
  2. washwashed with H20 (2×50 mL)
  3. extractionback extracted the aqueous phase
  4. washwashed
  5. dry with materialDried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-0c20773fc89c4d1e808adbafc2928f5d
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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