Water → HCID 22064029, compound

HRID 1017610Notes

Reaction equation

HRID 1017610 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[O:14][CH3:15].C([Li])CCC.C([O:23][CH2:24]C)C.[OH2:26]>O1CCCC1>[CH3:15][O:14][C:3]1[CH:4]=[C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:6]=[CH:7][C:2]=1[C:24]([OH:23])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 220640394-(4-Bromo-3-methoxyphenyl)morpholineHCID 178418339Butyllithium

Product 1

HCID 22064029HCID 22064029, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 4-bromo-3-methoxy-1-morpholinobenzene (104 mg, 0.382 mmol) in anhydrous tetrahydrofuran (3 mL) at −78° C. was slowly added n-butyl lithium (1.3 M solution in hexanes, 325 μL, 0.420 mmol) under nitrogen. The cooling medium was exchanged with an ice-bath, and the mixture was stirred for 5 min. After cooling again to −78° C., carbon dioxide from evaporation of dry ice was bubbled through the solution for 10 min. A precipitate was formed, and the reaction mixture was allowed to reach room temperature. Diethyl ether and water were added. The mixture was extracted, the layers were separated, and the aqueous layer was acidified to pH 4. The dark blue aqueous solution was extracted several times with diethyl ether and ethyl acetate at pH 4 to pH 6. The combined organic layers were dried (MgSO4), and the solvent was removed in vacuo affording 60 mg (66% yield) of the title compound as a white solid: mp 158-160° C.; EIMS m/z (relative intensity) 237 (100, M30 ).

Workup

  1. customat −78° C.
  2. customThe cooling medium was exchanged with an ice-bath
  3. customcarbon dioxide from evaporation of dry ice
  4. customwas bubbled through the solution for 10 min
  5. customA precipitate was formed
  6. customto reach room temperature
  7. extractionThe mixture was extracted
  8. customthe layers were separated
  9. extractionThe dark blue aqueous solution was extracted several times with diethyl ether and ethyl acetate at pH 4 to pH 6
  10. dry with materialThe combined organic layers were dried (MgSO4)
  11. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-64fd452edf534230b1c871da6a5fd63c
Source dataset
uspto-grants-2002_11
Patent number
US06479497B1

Reaction notes

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