Potassium Carbonate → HCID 20222106, compound

HRID 980164

Reaction equation

HRID 980164 reaction equation
[OH:1][CH:2]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)[CH2:3][NH:4][CH2:5][CH2:6][NH:7][C:8]([N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:9].S(O[CH2:30][CH2:31][O:32][CH3:33])(=O)(=O)C.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[OH:1][CH:2]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:30][CH2:31][O:32][CH3:33])=[CH:20][CH:19]=1)[CH2:3][NH:4][CH2:5][CH2:6][NH:7][C:8]([N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1462932-Methoxyethyl methanesulfonateHCID 155774Xamoterol

Product 1

HCID 20222106HCID 20222106, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

17 g of N-(2-((2-hydroxy-3-(4-hydroxyphenoxy)propyl)amino)ethyl)-4-morpholinecarboxamide and 6 g of 2-methoxyethyl mesylate and 6.9 g of K2CO3 was refluxed in acetonitril for 20 h. The resulting mixture was filtered and evaporated. The residue was dissolved in methylene chloride and extracted with water containing 1 g of NaOH, then with water and then dried over Na2SO4, filtered and evaporated. The residue was crystallized from ethyl acetate yielding N-(2-((2-hydroxy-3-(4-(2-methoxyethoxy)phenoxy)propyl)amino)ethyl)-4-morpholinecarboxamide. Melting point 69° C. (base).

Workup

  1. filtrationThe resulting mixture was filtered
  2. customevaporated
  3. dissolutionThe residue was dissolved in methylene chloride
  4. extractionextracted with water containing 1 g of NaOH
  5. dry with materialwith water and then dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-35a4833313734fafb83346fee0a81316
Source dataset
uspto-grants-1987_01
Patent number
US04636501

Linked notes

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