Acetic Acid → beta-Ethylaminoethylpyrazine

HRID 2052291Notes

Reaction equation

HRID 2052291 reaction equation
[CH:1]([C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1)=[CH2:2].[CH2:9]([NH2:11])[CH3:10].C(O)(=O)C.[OH-].[Na+]>O.CO>[CH2:9]([NH:11][CH2:2][CH2:1][C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1)[CH3:10]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6341EthylamineHCID 14798Sodium HydroxideHCID 77840Vinylpyrazine

Product 1

HCID 11073599beta-EthylaminoethylpyrazineYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 21.2 g (0.2 mole) of vinylpyrazine, 18.0 g (0.4 mole) of ethylamine, 6.0 g (0.1 mole) of acetic acid and 60 ml methanol was placed in a pressure bottle and heated at 70° C. for 24 hours. After removing the methanol, the residue was made basic with 8.0 g (0.2 mole) of sodium hydroxide in 80 ml of water and extracted with several portions of chloroform. After removing the chloroform, the residue was distilled to give 24.5 g of β-ethylaminoethylpyrazine, b.p. 70°-72° C. at 0.5 mm Hg, nD25 =1.5103.

Workup

  1. customAfter removing the methanol
  2. extractionextracted with several portions of chloroform
  3. customAfter removing the chloroform
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-0336519688cd478b8c78e7ebeea9ebaa
Source dataset
uspto-grants-1980_01
Patent number
US04183933

Reaction notes

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