Sulfate Ion → N-(2-((2-hydroxy-3-(4-(2-methoxyethoxy)phenoxy)propyl)amino)ethyl)-4-morpholinecarboxamide

HRID 980159Notes

Reaction equation

HRID 980159 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][CH:12]2[O:14][CH2:13]2)=[CH:8][CH:7]=1.S([O-])([O-])(=O)=O.[NH2:22][CH2:23][CH2:24][NH:25][C:26]([N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)=[O:27].C([O-])([O-])=O.[K+].[K+]>CC(O)C>[OH:14][CH:12]([CH2:11][O:10][C:9]1[CH:15]=[CH:16][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][CH:8]=1)[CH2:13][NH:22][CH2:23][CH2:24][NH:25][C:26]([N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)=[O:27]

Participants

6

Reactant 4

HCID 1117Sulfate IonHCID 11430Potassium CarbonateHCID 110411984-MorpholinecarboxaMide, N-(2-aMinoethyl)-HCID 126215491-(2,3-Epoxypropoxy)-4-(2-methoxyethoxy)benzene

Product 1

HCID 20222106N-(2-((2-hydroxy-3-(4-(2-methoxyethoxy)phenoxy)propyl)amino)ethyl)-4-morpholinecarboxamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4 g of 3-(4-(2-methoxyethoxy)phenoxy)-1,2-epoxypropane, 5.8 g of the sulphate of N-2-aminoethyl-4-morpholinecarboxamide, and 5.8 g of K2CO3 were refluxed in 2-propanol for 2 days. The mixture was filtered and concentrated in vacuo. The residue was dissolved in methylene chloride and washed with H2O. The organic phase was dried over Na2SO4, filtered and evaporated. The product was recrystallized from ethyl acetate. Yield 2.3 g. Melting point 69° C. (base). The structure was determined using NMR and equivalent weight.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed with H2O
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ef615be404514c78b21cfad46faf6846
Source dataset
uspto-grants-1987_01
Patent number
US04636501

Reaction notes

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