Water → 2-Methyl-1-[4-(4-morpholinyl)phenyl]-1-propanone

HRID 1743185Notes

Reaction equation

HRID 1743185 reaction equation
[CH2:1]([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1.O.[O:20]1[CH2:24][CH2:23][CH2:22]C1>>[CH3:22][CH:23]([CH3:1])[C:24]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1)=[O:20]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 116228514-(4-Bromophenyl)morpholineHCID 178418339Butyllithium

Product 1

HCID 222382912-Methyl-1-[4-(4-morpholinyl)phenyl]-1-propanoneYield 67%

Procedure

n-Butyllithium (1.6 M, 25.8 mL, 41.3 mmol) was added to a solution of 1-bromo-4-(4-morpholinyl)benzene (10.0 g, 41.3 mmol) in tetrahydrofuran (100 mL) at −78° C., and the mixture was stirred for 20 minutes at the same temperature. To the reaction mixture was added N-isobutyrylpropyleneimine (5.77 g, 45.4 mmol), and the mixture was stirred for 30 minutes at room temperature. Water (40 mL) was poured into the reaction mixture, which was then extracted twice with ethyl acetate. The organic layers were combined, washed with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was crystallized from hexane to obtain the title compound (6.50 g, yield 67%).

Workup

  1. stirringthe mixture was stirred for 30 minutes at room temperature
  2. extractionwas then extracted twice with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-f74c75408dad4a47be0b97dca8ca13e1
Source dataset
uspto-grants-2006_03
Patent number
US07008950B1

Reaction notes

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