Sodium hydride → HCID 14726735, compound

HRID 1198917Notes

Reaction equation

HRID 1198917 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:18]=[CH:17][C:7]([C:8](=[O:16])[CH2:9][NH:10][C:11](=[O:15])[O:12][CH2:13][CH3:14])=[CH:6][CH:5]=1.Cl[CH2:20][C:21]([NH:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[O:22]>CN(C)C=O>[O:29]1[CH2:28][CH2:27][N:26]([CH2:25][CH2:24][NH:23][C:21]([CH2:20][O:3][C:4]2[CH:18]=[CH:17][C:7]([C:8](=[O:16])[CH2:9][NH:10][C:11](=[O:15])[O:12][CH2:13][CH3:14])=[CH:6][CH:5]=2)=[O:22])[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 51590772-chloro-N-(2-morpholin-4-ylethyl)acetamideHCID 14099033HCID 14099033, compound

Product 1

HCID 14726735HCID 14726735, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

31 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) were added to a solution of 156 mg of ethyl N-(p-hydroxyphenacyl)carbamate (prepared as described in Preparation 6) dissolved in 10 ml of dimethylformamide. The mixture was then stirred at room temperature for 30 minute, after which 200 mg of 2-chloro-N-(2-morpholinoethyl)acetamide were added, and the mixture was stirred at 100° to 110° C. for 4 hours. The reaction mixture was then poured into ice-water and extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel eluted with ethyl acetate, to give 190 mg of the title compound as pale yellow needles melting at 133°-135° C.

Workup

  1. stirringthe mixture was stirred at 100° to 110° C. for 4 hours
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe residue was purified by column chromatography through silica gel
  7. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-6a4cc51d4ed1403fa6d63a3f71101cc1
Source dataset
uspto-grants-1990_02
Patent number
US04898862

Reaction notes

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