Dimethylamine → N-(4-dimethylamino-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide

HRID 1613280Notes

Reaction equation

HRID 1613280 reaction equation
Cl[CH2:2][C:3]#[C:4][CH2:5][NH:6][C:7](=[O:22])[C:8]([CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[I-].[Na+].[CH3:25][NH:26][CH3:27]>O1CCOCC1>[CH3:25][N:26]([CH3:27])[CH2:2][C:3]#[C:4][CH2:5][NH:6][C:7](=[O:22])[C:8]([CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5238Sodium IodideHCID 15023451N-(4-chloro-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide

Product 1

HCID 14931303N-(4-dimethylamino-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-(4-chloro-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide (0.5 g), sodium iodide (0.1 g), and 50% aqueous dimethylamine (1.5 ml) in 1,4-dioxane (5 ml) was stirred at room temperature overnight. After removal of the solvent, saturated sodium bicarbonate aqueous solution and ethyl acetate were added to the residue. The organic layer was separated, washed with sodium chloride aqueous solution, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform =nd methanol (20:1) as an eluent to give N-(4-dimethylamino-2-butynyl)-2-cyclohexyl -2-hydroxy-2-phenylacetamide (0.49 g) as oil.

Workup

  1. customAfter removal of the solvent, saturated sodium bicarbonate aqueous solution and ethyl acetate
  2. additionwere added to the residue
  3. customThe organic layer was separated
  4. washwashed with sodium chloride aqueous solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel with a mixture of chloroform =nd methanol (20:1) as an eluent

Sources & evidence

ORD record
ord-77306c71686e4e72bc5ecb31ea0fa396
Source dataset
uspto-grants-1993_03
Patent number
US05192779

Reaction notes

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