N-(2-aminoethyl)acetamide → HCID 19095413, compound

HRID 486528Notes

Reaction equation

HRID 486528 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=O)[CH2:11][CH2:12][CH:13]3OC=CO3)=[CH:9][C:4]=2[O:3][CH2:2]1.[C:19]([NH:22][CH2:23][CH2:24][NH2:25])(=[O:21])[CH3:20]>C(O)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:25]([CH2:24][CH2:23][NH:22][C:19](=[O:21])[CH3:20])[CH:13]=[CH:12][CH:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 19095270HCID 19095270, compound

Product 1

HCID 19095413HCID 19095413, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(1,3-Benzodioxol-5-yl)-3-(1,3-dioxol-2-yl)-1-propanone (1.7 g) was added under argon and while stirring to a solution of 1.4 g of N-acetylethylenediamine in 20 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 80 ml of methylene chloride and washed with a mixture of 50 ml of saturated sodium hydrogen carbonate solution and 10 ml of 2N sodium hydroxide solution. The aqueous phase was back-extracted twice with 50 ml of methylene chloride each time, the organic phases were combined, dried with MgSO4 and freed from solvent. The residue, 2.6 g of brown oil, was chromatographed on 50 g of silica gel with ethyl acetate/hexane (2:1) as the eluent. 1.7 g (95%) of N-[2-[2-(1,3-benzodioxol-5-yl)-pyrrol-1-yl]-ethyl]acetamide were isolated as a yellow oil. MS: m/e=272 (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 50 ml of saturated sodium hydrogen carbonate solution and 10 ml of 2N sodium hydroxide solution
  4. extractionThe aqueous phase was back-extracted twice with 50 ml of methylene chloride each time
  5. dry with materialdried with MgSO4
  6. customThe residue, 2.6 g of brown oil, was chromatographed on 50 g of silica gel with ethyl acetate/hexane (2:1) as the eluent

Sources & evidence

ORD record
ord-f7f77ffe22fa405383c798728e6f7ea4
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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