Morpholine → HCID 15547736, compound

HRID 2090922Notes

Reaction equation

HRID 2090922 reaction equation
Cl[CH2:2][C:3](=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>O1CCCC1>[N:10]1([CH2:2][C:3](=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 36240Methyl 4-chloroacetoacetate

Product 1

HCID 15547736HCID 15547736, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (300 mL) of methyl 4-chloro-3-oxobutanoate (27.1 g) in tetrahydrofuran was added morpholine (34.5 g) under ice-cooling. The ice bath was removed, and the reaction mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, 1N hydrochloric acid (100 mL) was added, and the mixture was extracted with diethyl ether. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10, volume ratio) to give the title object compound (12.8 g, 35%) as a yellow oil.

Workup

  1. temperaturecooling
  2. customThe ice bath was removed
  3. customThe solvent was evaporated under reduced pressure, 1N hydrochloric acid (100 mL)
  4. additionwas added
  5. extractionthe mixture was extracted with diethyl ether
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10, volume ratio)

Sources & evidence

ORD record
ord-12b52d644a594bd6b253fd24a2a5c753
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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