N-(2-aminoethyl)acetamide → HCID 19095279, compound

HRID 486524Notes

Reaction equation

HRID 486524 reaction equation
O1CCO[CH:2]1[CH2:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)=O.[C:17]([NH:20][CH2:21][CH2:22][NH2:23])(=[O:19])[CH3:18]>C(O)(=O)C>[C:13]1([CH3:16])[CH:12]=[CH:11][C:10]([C:8]2[N:23]([CH2:22][CH2:21][NH:20][C:17](=[O:19])[CH3:18])[CH:2]=[CH:6][CH:7]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 19095369HCID 19095369, compound

Product 1

HCID 19095279HCID 19095279, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

3-(1,3-Dioxolan-2yl)-4'-methylpropiophenone (10.2 g) was dissolved in 20 ml of acetic acid and added under argon and while stirring to a solution of 9.4 g of N-acetylethylenediamine in 100 ml of acetic acid. The reaction mixture was heated to reflux overnight, the acetic acid was subsequently removed in a vacuum. The residue was taken up in 200 ml of methylene chloride and washed with a mixture of 100 ml of saturated sodium hydrogen carbonate solution and 150 ml of 2N sodium hydroxide solution. The aqueous phase was back-extracted twice with 100 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. The residue, 14.0 g of dark brown oil were chromatographed on 550 g of silica gel with ethyl acetate/hexane (2:1) as the eluent. 7.8 g (70%) of N-[2-(2-p-tolylpyrrol-1-yl)ethyl]acetamide were isolated as a brown oil. MS: m/e=242 (M+).

Workup

  1. additionadded under argon
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux overnight
  4. customthe acetic acid was subsequently removed in a vacuum
  5. washwashed with a mixture of 100 ml of saturated sodium hydrogen carbonate solution and 150 ml of 2N sodium hydroxide solution
  6. extractionThe aqueous phase was back-extracted twice with 100 ml of methylene chloride each time
  7. dry with materialdried with MgSO4
  8. customThe residue, 14.0 g of dark brown oil were chromatographed on 550 g of silica gel with ethyl acetate/hexane (2:1) as the eluent

Sources & evidence

ORD record
ord-54bd2f700d3c41b7a2f8712626a99509
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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