Sodium Bicarbonate → N-(4-diethylamino-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide

HRID 1613287Notes

Reaction equation

HRID 1613287 reaction equation
Cl.[CH2:2]([N:4]([CH2:26][CH3:27])[CH2:5][C:6]#[C:7][CH2:8][NH:9][C:10](=[O:25])[C:11](Cl)([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:3].C(=O)(O)[O-:29].[Na+]>O>[CH2:2]([N:4]([CH2:26][CH3:27])[CH2:5][C:6]#[C:7][CH2:8][NH:9][C:10](=[O:25])[C:11]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)([OH:29])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:3]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 19775490N-(4-diethylamino-2-butynyl)-2-chloro-2-cyclohexyl-2-phenylacetamide hydrochloride

Product 1

HCID 14931302N-(4-diethylamino-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(4-Diethylamino-2-butynyl)-2-chloro-2-cyclohexyl-2-phenylacetamide hydrochloride (100 mg) was dissolved in water (1 ml) and the solution was refluxed for 20 minutes. After being cooled, the solution was made alkaline (pH 10) with saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate. The extract was washed with sodium chloride aqueous solution, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol as an eluent to give N-(4-diethylamino-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide (74 mg).

Workup

  1. temperaturethe solution was refluxed for 20 minutes
  2. temperatureAfter being cooled
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with sodium chloride aqueous solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol as an eluent

Sources & evidence

ORD record
ord-a366e5e07fcd47ab9411e032db897c9e
Source dataset
uspto-grants-1993_03
Patent number
US05192779

Reaction notes

Loading…