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

HRID 980162Notes

Reaction equation

HRID 980162 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+].[CH:20]1([CH2:24][O:25][CH2:26][CH2:27][O:28][C:29]2[CH:39]=[CH:38][C:32]([O:33][CH:34]3[O:37][CH:35]3[CH3:36])=[CH:31][CH:30]=2)[CH2:23][CH2:22][CH2:21]1>C(O)C>[OH:37][CH:35]([CH2:34][O:33][C:32]1[CH:38]=[CH:39][C:29]([O:28][CH2:27][CH2:26][O:25][CH2:24][CH:20]2[CH2:23][CH2:22][CH2:21]2)=[CH:30][CH:31]=1)[CH2:36][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 867412074-(2-Cyclobutylmethoxyethoxy)phenoxy-1,2-epoxypropane

Product 1

HCID 20222111N-(2-((2-hydroxy-3-(4-(2-cyclobutylmethoxyethoxy)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 and 2.16 g NaOH was refluxed in 100 ml of ethanol for 1 h. Thereafter 10 g of 3-(4-(2-cyclobutylmethoxyethoxy)phenoxy-1,2-epoxypropane in 50 ml of ethanol was added and the mixture refluxed for 20 h, filtered, and evaporated. The residue was dissolved in 175 ml of ethyl acetate and washed twice with water. Thereafter the title compound crystallized from the ethyl acetate phase. The crystals were filtered off and washed with ether. Yield 7.1 g. Melting point 91°-93° C. (base). The structure was determined using NMR-analysis.

Workup

  1. temperaturethe mixture refluxed for 20 h
  2. filtrationfiltered
  3. customevaporated
  4. dissolutionThe residue was dissolved in 175 ml of ethyl acetate
  5. washwashed twice with water
  6. customThereafter the title compound crystallized from the ethyl acetate phase
  7. filtrationThe crystals were filtered off
  8. washwashed with ether

Sources & evidence

ORD record
ord-5c5a26d1ff074d4784a66c18afa989e5
Source dataset
uspto-grants-1987_01
Patent number
US04636501

Reaction notes

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