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

HRID 980160Notes

Reaction equation

HRID 980160 reaction equation
S([O-])([O-])(=O)=O.[NH2:6][CH2:7][CH2:8][NH:9][C:10]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[O:11].[OH-].[Na+].[CH2:20]([O:22][CH2:23][CH2:24][O:25][C:26]1[CH:36]=[CH:35][C:29]([O:30][CH:31]2[O:34][CH:32]2[CH3:33])=[CH:28][CH:27]=1)[CH3:21]>C(O)C>[OH:34][CH:32]([CH2:31][O:30][C:29]1[CH:35]=[CH:36][C:26]([O:25][CH2:24][CH2:23][O:22][CH2:20][CH3:21])=[CH:27][CH:28]=1)[CH2:33][NH:6][CH2:7][CH2:8][NH:9][C:10]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[O:11]

Participants

6

Reactant 4

HCID 1117Sulfate IonHCID 14798Sodium HydroxideHCID 11041198N-(2-Aminoethyl)-4-morpholinecarboxamideHCID 867412064-(2-Ethoxyethoxy)phenoxy-1,2-epoxypropane

Product 1

HCID 20222117N-(2-((2-hydroxy-3-(4-(2-ethoxyethoxy)-phenoxy)propyl)amino)ethyl)-4-morpholinecarboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

12.0 g of the neutral sulphate of N-2-aminoethyl-4-morpholinecarboxamide, 2.16 g NaOH and 100 ml of absolute ethanol were refluxed 1 h. During continuing reflux 8.6 g of 3-(4-(2-ethoxyethoxy)phenoxy-1,2-epoxypropane in 50 ml of abs. ethanol was added little by little. The resulting mixture was refluxed over night, filtered and evaporated. The residue was dissolved in 200 ml of ethyl acetate and extracted twice with water. The water phase was treated with NaCl and extracted twice with ethyl acetate. The ethyl acetate phase was dried, filtered and evaporated. The residue was crystallized from ether, and recrystallized from ethyl acetate. Yield 1.1 g. Melting point 75°-77° C. (base). The structure was determined using NMR analysis.

Workup

  1. temperatureThe resulting mixture was refluxed over night
  2. filtrationfiltered
  3. customevaporated
  4. dissolutionThe residue was dissolved in 200 ml of ethyl acetate
  5. extractionextracted twice with water
  6. additionThe water phase was treated with NaCl
  7. extractionextracted twice with ethyl acetate
  8. dry with materialThe ethyl acetate phase was dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was crystallized from ether
  12. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-150ac62b6e6f4b6b966759c6249fdc88
Source dataset
uspto-grants-1987_01
Patent number
US04636501

Reaction notes

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