Hydrochloric Acid → N-(2-((2-hydroxy-3-(4-(2-cyclopropylmethoxyethoxy)phenoxy)propyl)amino)ethyl)-4-morpholinecarboxamide

HRID 980161Notes

Reaction equation

HRID 980161 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][NH:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:7].[OH-].[Na+].[CH:16]1([CH2:19][O:20][CH2:21][CH2:22][O:23][C:24]2[CH:34]=[CH:33][C:27]([O:28][CH2:29][CH:30]3[O:32][CH2:31]3)=[CH:26][CH:25]=2)[CH2:18][CH2:17]1>C(O)C>[OH:32][CH:30]([CH2:29][O:28][C:27]1[CH:33]=[CH:34][C:24]([O:23][CH2:22][CH2:21][O:20][CH2:19][CH:16]2[CH2:18][CH2:17]2)=[CH:25][CH:26]=1)[CH2:31][NH:2][CH2:3][CH2:4][NH:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11041198N-(2-Aminoethyl)-4-morpholinecarboxamideHCID 150353032-((4-(2-(Cyclopropylmethoxy)ethoxy)phenoxy)methyl)oxirane

Product 1

HCID 21289591N-(2-((2-hydroxy-3-(4-(2-cyclopropylmethoxyethoxy)phenoxy)propyl)amino)ethyl)-4-morpholinecarboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

26.2 g of the hydrochloride of N-2-aminoethyl-4-morpholinecarboxamide and 5.0 g of NaOH were refluxed in 175 ml of ethanol for 1 h. Thereafter 22 g of 3-(4-(2-cyclopropylmethoxyethoxy)phenoxy)-1,2-epoxypropane in 100 ml of ethanol was added and the resulting mixture refluxed for 16 h, filtered, and evaporated. The residue was dissolved in 300 ml of ethyl acetate and washed three times with water. The organic phase was then extracted with 250 ml of water at pH 5 (HCl). The aqueous phase was then made alkaline and extracted with methylene chloride. The methylene chloride phase was dried over Na2SO4, filtered, and evaporated. The residue was treated with ether and recrystallized from ethyl acetate. Yield 8.0 g. Melting point 80°-81° C. (base). The structure was determined using NMR-analysis.

Workup

  1. temperaturethe resulting mixture refluxed for 16 h
  2. filtrationfiltered
  3. customevaporated
  4. dissolutionThe residue was dissolved in 300 ml of ethyl acetate
  5. washwashed three times with water
  6. extractionThe organic phase was then extracted with 250 ml of water at pH 5 (HCl)
  7. extractionextracted with methylene chloride
  8. dry with materialThe methylene chloride phase was dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated
  11. additionThe residue was treated with ether
  12. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2ae0810d2a5c45a7a72e790ac9abc023
Source dataset
uspto-grants-1987_01
Patent number
US04636501

Reaction notes

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