Dimethylamine → HCID 14931313, compound

HRID 1613283Notes

Reaction equation

HRID 1613283 reaction equation
Cl[CH2:2][C:3]#[C:4][CH2:5][NH:6][C:7](=[O:22])[C:8]([OH:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[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]([OH:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5238Sodium IodideHCID 15023455HCID 15023455, compound

Product 1

HCID 14931313HCID 14931313, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-(4-chloro-2-butynyl)-2-hydroxy-2,2-diphenylacetamide (0.70 g), sodium iodide (0.1 g) and 50% aqueous dimethylamine (2.2 ml) in 1,4-dioxane (7 ml) was stirred at room temperature overnight and then evaporated in vacuo. After an addition of saturated sodium bicarbonate aqueous solution, the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (20:1) as an eluent to give N-(4-dimethylamino-2-butynyl)-2-hydroxy-2,2-diphenylacetamide (0.35 g).

Workup

  1. customevaporated in vacuo
  2. additionAfter an addition of saturated sodium bicarbonate aqueous solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  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 and methanol (20:1) as an eluent

Sources & evidence

ORD record
ord-758661b023714ae3a872db046b42f551
Source dataset
uspto-grants-1993_03
Patent number
US05192779

Reaction notes

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