Ethylamine → HCID 14931314, compound

HRID 973990Notes

Reaction equation

HRID 973990 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 (5:1) as an eluent

Sources & evidence

ORD record
ord-eee0a846ab284592b0ad3975db560602
Source dataset
uspto-grants-1991_11
Patent number
US05066680

Reaction notes

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