Acetylpyrazine → 1-(Pyrazin-2-yl)ethanamine

HRID 1669868Notes

Reaction equation

HRID 1669868 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7](=O)[CH3:8].C([O-])(=O)C.[NH4+:14]>CO.C([BH3-])#N.[Na+]>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH:7]([NH2:14])[CH3:8]

Participants

5

Reactant 2

HCID 30914AcetylpyrazineHCID 517165Ammonium Acetate

Product 1

HCID 185190061-(Pyrazin-2-yl)ethanamineYield 749%

Reagents, catalysts & solvents 2

HCID 5003444Sodium cyanoborohydrideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-pyrazin-2-yl-ethanone (2.0 g, 15.85 mmol) and ammonium acetate (19.337 g, 158.5 mmol) in methanol (50 mL) was added sodium cyanoborohydride (0.7 g, 11.1 mmol) in one portion. The reaction mixture was stirred overnight at room temperature. After removal of methanol, water (20 mL) was added to the residue and the resulting solution was basified by addition of sodium hydroxide to pH=13. The aqueous solution was extracted with dicholromethane and the combined organic phase was dried over sodium sulfate. Removal of the solvent under reduced pressure afforded 14.62 g of 1-pyrazin-2-yl-ethylamine, yield: 75%. MS (M+H)=124.

Workup

  1. customAfter removal of methanol, water (20 mL)
  2. additionwas added to the residue
  3. additionthe resulting solution was basified by addition of sodium hydroxide to pH=13
  4. extractionThe aqueous solution was extracted with dicholromethane
  5. dry with materialthe combined organic phase was dried over sodium sulfate
  6. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-005695daeecc45a7a1fff943858ef1a7
Source dataset
uspto-grants-2011_08
Patent number
US07989637B2

Reaction notes

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