N-(2-aminoethyl)acetamide → HCID 19095305, compound

HRID 486574Notes

Reaction equation

HRID 486574 reaction equation
O1CCO[CH:2]1[CH2:6][CH:7]([CH3:16])[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O.[C:17]([NH:20][CH2:21][CH2:22][NH2:23])(=[O:19])[CH3:18]>C(O)(=O)C>[CH3:16][C:7]1[CH:6]=[CH:2][N:23]([CH2:22][CH2:21][NH:20][C:17](=[O:19])[CH3:18])[C:8]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 21803382HCID 21803382, compound

Product 1

HCID 19095305HCID 19095305, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-(1,3-Dioxolan-2-yl)-2-methylpropiophenone (7.1 g) was added to a solution of 6.6 g of N-acetylethylenediamine in 100 ml of acetic acid under argon and while stirring. The reaction solution was boiled for 18 hours and 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 160 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, 7.6 g of brown oil was chromatographed on 350 g of silica gel with ethyl acetate/hexane mixtures (1:3 to 2:1) as the eluent. 4.6 g (59%) of N-[2-[3-methyl-2-phenylpyrrol-1-yl]ethyl]acetamide were isolated as a brown, amorphous solid. MS: m/e=242 (M+ ).

Workup

  1. customthe acetic acid was subsequently removed in a vacuum
  2. washwashed with a mixture of 100 ml of saturated sodium hydrogen carbonate solution and 160 ml of 2N sodium hydroxide solution
  3. extractionThe aqueous phase was back-extracted twice with 100 ml of methylene chloride each time
  4. dry with materialdried with MgSO4
  5. customThe residue, 7.6 g of brown oil was chromatographed on 350 g of silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-3b3393d4a07c4d6190de74a680283ef0
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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