N-(2-aminoethyl)acetamide → HCID 19095412, compound

HRID 486531Notes

Reaction equation

HRID 486531 reaction equation
O1CCO[CH:2]1[CH2:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)=O.[C:20]([NH:23][CH2:24][CH2:25][NH2:26])(=[O:22])[CH3:21]>C(O)(=O)C>[CH3:19][O:18][C:12]1[CH:11]=[C:10]([C:8]2[N:26]([CH2:25][CH2:24][NH:23][C:20](=[O:22])[CH3:21])[CH:2]=[CH:6][CH:7]=2)[CH:15]=[CH:14][C:13]=1[O:16][CH3:17]

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 19095326HCID 19095326, compound

Product 1

HCID 19095412HCID 19095412, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

3-(1,3-Dioxolan-2-yl)-3',4'-dimethoxypropiophenone (6.3 g) was dissolved in 30 ml of acetic acid and added under argon and while stirring to a solution of 4.9 g of N-acetylethylenediamine in 50 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 150 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 three times with 100 ml of methylene chloride each time, the organic phases were combined, dried with MgSO4 and freed from solvent. The residue, 7.3 g of dark brown oil, was chromatographed on 250 g of silica gel with ethyl acetate as the eluent. 2.6 g (38%) of N-[2-[2-(3,4-dimethoxyphenyl)pyrrol-1-yl]-ethyl]acetamide were isolated as a brown oil.

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 three times with 100 ml of methylene chloride each time
  7. dry with materialdried with MgSO4
  8. customThe residue, 7.3 g of dark brown oil, was chromatographed on 250 g of silica gel with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-1e91fa90bb644d91ab87249a6052a102
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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