Glutaric anhydride → 5-Morpholin-4-YL-5-oxopentanoic acid

HRID 1820928Notes

Reaction equation

HRID 1820928 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>O1CCCC1>[N:9]1([C:5](=[O:6])[CH2:4][CH2:3][CH2:2][C:1]([OH:7])=[O:8])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 7940Glutaric anhydrideHCID 8083Morpholine

Product 1

HCID 157799485-Morpholin-4-YL-5-oxopentanoic acidYield 52.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Glutaric anhydride (1.14 g) is dissolved in tetrahydrofuran (20 ml), and thereto is added morpholine (0.87 g). The mixture is then stirred at room temperature for 19 hours. The reaction solution is concentrated under reduced pressure, and the residue is diluted with chloroform and washed with 10% hydrochloric acid. The organic layer is dried over sodium sulfate and evaporated to remove the solvent under reduced pressure to give the title compound (1.05 g). ESI-MS M/Z:200[M−H]−

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. additionthe residue is diluted with chloroform
  3. washwashed with 10% hydrochloric acid
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-8068c06d12f64222b524caeda8fc439e
Source dataset
uspto-grants-2009_10
Patent number
US07605158B2

Reaction notes

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