N-(2-aminoethyl)acetamide → N-[2-[2-(4-Methoxyphenyl)-1H-pyrrol-1-yl]ethyl]acetamide

HRID 486516Notes

Reaction equation

HRID 486516 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])=[CH:12][CH:11]=1)=O.[C:18]([NH:21][CH2:22][CH2:23][NH2:24])(=[O:20])[CH3:19]>C(O)(=O)C>[CH3:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([C:8]2[N:24]([CH2:23][CH2:22][NH:21][C:18](=[O:20])[CH3:19])[CH:2]=[CH:6][CH:7]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 2758698HCID 2758698, compound

Product 1

HCID 19095262N-[2-[2-(4-Methoxyphenyl)-1H-pyrrol-1-yl]ethyl]acetamideYield 66%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

3-(1,3-Dioxolan-2-yl)-4'-methoxypropiophenone (38.8 g) was dissolved in 100 ml of acetic acid and added under argon and while stirring to a solution of 33.5 g of N-acetylethylene-diamine in 500 ml of acetic acid. The reaction solution was heated to reflux overnight, the acetic acid was subsequently removed in a vacuum. The residue was taken up in 500 ml of methylene chloride and washed with a mixture of 200 ml of saturated sodium hydrogen carbonate solution and 400 ml of 2N sodium hydroxide solution. The aqueous phase was 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, 49.6 g of brown oil, was chromatographed on 500 g of silica gel with ethyl acetate as the eluent. 27.8 g (66%) of N-[2-[2-(p-methoxyphenyl)-pyrrol-1-yl]ethyl]acetamide were isolated as a yellow-brown oil. MS: m/e=258 (M+).

Workup

  1. additionadded under argon
  2. temperatureThe reaction solution was heated
  3. temperatureto reflux overnight
  4. customthe acetic acid was subsequently removed in a vacuum
  5. washwashed with a mixture of 200 ml of saturated sodium hydrogen carbonate solution and 400 ml of 2N sodium hydroxide solution
  6. extractionThe aqueous phase was extracted three times with 100 ml of methylene chloride each time
  7. dry with materialdried with MgSO4
  8. customThe residue, 49.6 g of brown oil, was chromatographed on 500 g of silica gel with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-c396bebceea34032bd95339678bef84d
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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