N-(2-aminoethyl)acetamide → Acetamide,n-[2-[2-[4-(trifluoromethyl)phenyl]-1h-pyrrol-1-yl]ethyl]-

HRID 486518Notes

Reaction equation

HRID 486518 reaction equation
O1CCO[CH:2]1[CH2:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)=O.[C:20]([NH:23][CH2:24][CH2:25][NH2:26])(=[O:22])[CH3:21]>C(O)(=O)C>[F:19][C:16]([F:17])([F:18])[C:13]1[CH:12]=[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]=1

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 27587083-(1,3-Dioxolan-2-yl)-1-(4-(trifluoromethyl)phenyl)propan-1-one

Product 1

HCID 19095353Acetamide,n-[2-[2-[4-(trifluoromethyl)phenyl]-1h-pyrrol-1-yl]ethyl]-Yield 78.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-(1,3-Dioxolan-2-yl)-4'-(trifluoromethyl)-propiophenone (6.4 g) was added under argon and while stirring to a solution of 4.8 g of N-acetylethylenediamine in 70 ml of acetic acid. The reaction mixture was refluxed 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 70 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, 9.4 g of yellow-brown solid was chromatographed on 500 g of silica gel with ethyl acetate as the eluent. 5.4 g (78%) of N-[2-[2-[4-(trifluoromethyl)phenyl]-pyrrol-1-yl]ethyl]acetamide were isolated as a yellow amorphous solid. MS: m/e=296 (M+).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customthe acetic acid was subsequently removed in a vacuum
  3. washwashed with a mixture of 100 ml of saturated sodium hydrogen carbonate solution and 70 ml of 2N sodium hydroxide solution
  4. extractionThe aqueous phase was back-extracted twice with 100 ml of methylene chloride each time
  5. dry with materialdried with MgSO4
  6. customThe residue, 9.4 g of yellow-brown solid was chromatographed on 500 g of silica gel with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-6735def2d86b432c842741ea90179ca9
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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