Morpholine → 2-Methylene4-morpholin-4-yl-4-oxo-butyric acid

HRID 1796132Notes

Reaction equation

HRID 1796132 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7]1(=[O:14])[O:13][C:11](=[O:12])[CH2:10][C:8]1=[CH2:9]>ClCCl>[CH2:9]=[C:8]([CH2:10][C:11]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:12])[C:7]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 75110Itaconic Anhydride

Product 1

HCID 220540222-Methylene4-morpholin-4-yl-4-oxo-butyric acidYield 68.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Morpholine (23.6 g, 271 mmol) was slowly added to a stirred solution of itaconic anhydride (30.36 g, 271 mmol) suspended in dichloromethane (200 mL) below −5° C. and stirred at that temperature for 1 hr. The reaction mixture was allowed to slowly warm up to room temperature and evaporated under reduced pressure below 30° C. to give a viscous oil. This was triturated with ethyl acetate to give 2-Methylene-4-morpholin-4-yl-4-oxo-butyric acid as white solid (36.8 g, 68%). The product was used without further purification in the next step.

Workup

  1. customevaporated under reduced pressure below 30° C.
  2. customto give a viscous oil
  3. customThis was triturated with ethyl acetate

Sources & evidence

ORD record
ord-f8e0b9e4649b4bfbb7b4354fe84e8b96
Source dataset
uspto-grants-2006_04
Patent number
US07030116B2

Reaction notes

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