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

HRID 1642288Notes

Reaction equation

HRID 1642288 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 dichloromethane 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
  4. extractionThe aqueous solution was extracted with dichloromethane
  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-ffd9174f10cd45e196108a108459c070
Source dataset
uspto-grants-2012_02
Patent number
US08119644B2

Reaction notes

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