Triethylamine → N-(1-Hydroxy-1-phenylpropan-2-yl)morpholine-4-carboxamide

HRID 972186

Reaction equation

HRID 972186 reaction equation
[CH3:1][C@@H:2]([NH2:11])[C@@H:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[N:19]1([C:25](Cl)=[O:26])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>C(Cl)Cl>[CH3:1][CH:2]([NH:11][C:25]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[O:26])[CH:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[OH:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26934(1S,2R)-2-amino-1-phenylpropan-1-olHCID 848104-Morpholinecarbonyl chloride

Product 1

HCID 20314573N-(1-Hydroxy-1-phenylpropan-2-yl)morpholine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 15.2 grams of norephedrine in 200 ml. of CH2Cl2 was cooled to 0-5° C. To this 11.0 grams of triethylamine was added with stirring. To the stirred mixture a solution of 14.9 grams of morpholine carbonyl chloride in 10 ml. of CH2Cl2 was added dropwise. The mixture was then stirred for 2 hours and left to stand at room temperature for 16 hours. The mixture was washed with water and the organic layer was dried over anhydrous sodium sulfate. The organic layer was then filtered and evaporated to a small volume. The hydroxyethylurea, N-(1-methyl-2-phenyl-2-hydroxyethyl)-4-morpholinecarboxamide was filtered off as a white solid and recrystallized from CH2Cl2.

Workup

  1. stirringThe mixture was then stirred for 2 hours
  2. waitleft
  3. washThe mixture was washed with water
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationThe organic layer was then filtered
  6. customevaporated to a small volume
  7. filtrationThe hydroxyethylurea, N-(1-methyl-2-phenyl-2-hydroxyethyl)-4-morpholinecarboxamide was filtered off as a white solid
  8. customrecrystallized from CH2Cl2

Sources & evidence

ORD record
ord-ed79c1d3c9994505a65458bd5210e790
Source dataset
uspto-grants-1977_10
Patent number
US04052385

Linked notes

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