Morpholine → HCID 67429791, compound

HRID 1662736

Reaction equation

HRID 1662736 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOC(C)=O.O>[Br:1][C:2]1[CH:7]=[C:6]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:5]=[CH:4][C:3]=1[O:9][CH3:10]

Participants

9

Reactant 4

HCID 8083MorpholineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 33767792-Bromo-4-iodoanisoleHCID 23676156Sodium t-butoxide

Product 1

HCID 67429791HCID 67429791, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

Under nitrogen atmosphere, to a solution of 20.0 g of 2-bromo-4-iodoanisole in toluene (250 ml) was added morpholine (6.12 ml), 1.29 g of tri-tert-butyl phosphine, 13.5 g of sodium tert-butoxide, and 359 mg of palladium acetate (II), and the reaction mixture was stirred for two hours at 45° C. Water and EtOAc were added to the reaction solution, liquid separation was performed and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with saturated brine, dried over MgSO4, then, the drying agent was separated by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (Chromatorex NH; mobile phase: n-hexane/EtOAc=10/1 to 3/1; v/v) to obtain 3.94 g of the title compound (colorless powder).

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over MgSO4
  4. customthe drying agent was separated by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by column chromatography (Chromatorex NH; mobile phase: n-hexane/EtOAc=10/1 to 3/1; v/v)

Sources & evidence

ORD record
ord-ed2204e738f3451d964cad9d09492659
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Linked notes

Loading…