Morpholine → 4-Morpholineacetic acid

HRID 21687

Reaction equation

HRID 21687 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 (leq) 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 ace tare. 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 (D2O) 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 ace tare
  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-74699f098ef346148787f0d4580594ae
Source dataset
uspto-grants-1995_06
Patent number
US05424425

Linked notes

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