Ethylamine → HCID 14931314, compound

HRID 1613285Notes

Reaction equation

HRID 1613285 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.[CH2:23]([NH2:25])[CH3:24]>CO>[CH2:23]([NH:25][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)[CH3:24]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 15023455HCID 15023455, compound

Product 1

HCID 14931314HCID 14931314, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(4-chloro-2-butynyl)-2-hydroxy-2,2-diphenylacetamide (1.0 g) and 70% aqueous ethylamine (4.32 g) in methanol (3 ml) was stirred at room temperature for 30 minutes and then evaporated in vacuo. The residue was dissolved in chloroform (30 ml) and the solution was 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 and methanol (5:1}as an eluent to give N-(4-ethylamino-2-butynyl)-2-hydroxy-2,2-diphenylacetamide (0.8 g), which was treated with 4N methanolic hydrogen chloride to give N-(4-ethylamino-2-butynyl)-2-hydroxy-2,2-diphenylacetamide hydrochloride (0.65 g).

Workup

  1. customevaporated in vacuo
  2. dissolutionThe residue was dissolved in chloroform (30 ml)
  3. washthe solution was washed with sodium chloride aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (5

Sources & evidence

ORD record
ord-7698e1186d0c402182e5aed2c1087b2b
Source dataset
uspto-grants-1993_03
Patent number
US05192779

Reaction notes

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