Morpholine → 4-Morpholineacetic acid

HRID 260671Notes

Reaction equation

HRID 260671 reaction equation
Br[CH2:2][C:3]([O:5]C(C)(C)C)=[O:4].[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>O1CCCC1>[O:13]1[CH2:14][CH2:15][N:10]([CH2:2][C:3]([OH:5])=[O:4])[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 79177tert-Butyl bromoacetate

Product 1

HCID 4389684-Morpholineacetic acidYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve t-butyl bromoacetate (1 eq) in tetrahydrofuran and add morpholine (2.2 eq) via syringe. Stir the reaction mixture at room temperature for 2 hours, filter and wash the filter cake with ethyl acetate. Combine the organic filtrates and wash with saturated sodium bicarbonate (2×), water (2×) and brine. Dry (Na2SO4), filter and evaporate the solvent in vacuo. Take up the oily residue in ethyl acetate, cool in ice and bubble hydrogen chloride gas into the solution. Stir at room temperature overnight, cool and filter to give morpholinoacetic acid (85%); mp 169°-170° C.; 1H NMR (D20) δ3.75-4.29 (br m, 6), 3.59 (br s, 2), 3.28 (br s, 2).

Workup

  1. filtrationfilter
  2. washwash the filter cake with ethyl acetate
  3. washwash with saturated sodium bicarbonate (2×), water (2×) and brine
  4. dry with materialDry (Na2SO4)
  5. filtrationfilter
  6. customevaporate the solvent in vacuo
  7. temperaturecool in ice
  8. custombubble hydrogen chloride gas into the solution
  9. stirringStir at room temperature overnight
  10. temperaturecool
  11. filtrationfilter

Sources & evidence

ORD record
ord-12d5938b709f4c80b99bb77d611e56c1
Source dataset
uspto-grants-1996_06
Patent number
US05529995

Reaction notes

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