Water → HCID 53637089, compound

HRID 1816757Notes

Reaction equation

HRID 1816757 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8](F)=[CH:7][CH:6]=1)[CH3:2].[CH3:13][C@H:14]1[O:19][C@@H:18]([CH3:20])[CH2:17][NH:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([N:16]2[CH2:15][C@H:14]([CH3:13])[O:19][C@H:18]([CH3:20])[CH2:17]2)=[CH:7][CH:6]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 6415002,6-Dimethylmorpholine, cis-

Product 1

HCID 53637089HCID 53637089, compoundYield 11.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-fluorobenzoic acid ethyl ester (3 g), cis-2,6-dimethylmorpholine (2.26 g) and potassium carbonate (2.47 g) in dimethylsulfoxide (60 ml) was stirred for 18 hours at 80° C. The reaction mixture was added to a mixture of water and ethyl acetate. The organic layer was taken and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (5:1 hexane-ethyl acetate elution) to give 4-(cis-2,6-dimethylmorpholin-4-yl)benzoic acid ethyl ester (555 mg).

Workup

  1. dry with materialdried over magnesium sulfate
  2. filtrationThe magnesium sulfate was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (5:1 hexane-ethyl acetate elution)

Sources & evidence

ORD record
ord-53b913d8db2944c48fae8bcea5e0e362
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

Loading…