Morpholine → 4-Morpholineacetic acid

HRID 54926

反応式

HRID 54926 の反応式
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

参加物

4

反応物 2

HCID 8083MorpholineHCID 79177tert-Butyl bromoacetate

生成物 1

HCID 4389684-Morpholineacetic acid収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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 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 (D2O) δ3.75-4.29 (br m, 6), 3.59 (br s, 2), 3.28 (br s, 2).

後処理

  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

出典と根拠

ORDレコード
ord-41122aec198441e299be45521007238b
出典データセット
uspto-grants-1997_04
特許番号
US05624921

関連ノート

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