4-Methoxybenzylamine → HCID 22248994, compound

HRID 889872Notes

Reaction equation

HRID 889872 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1>C(O)C>[Cl:8][C:4]1[N:3]=[C:2]([NH:16][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[CH:7]=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 785042,6-Dichloropyrazine

Product 1

HCID 22248994HCID 22248994, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
115 °C

Procedure

To a stirred solution of 2,6-dichloropyrazine (25 g, 0.167 mol) and ethanol (120 mL) in a sealed tube is added 4-methoxybenzylamine (68.6 g, 0.5 mol). The mixture is heated to 115° C. for 12 h and cooled. The white solid is removed by filtration and the filtrate evaporated. The residue is dissolved in ethyl acetate and washed successively with 2 M sodium hydroxide, water and aqueous sodium chloride. The organics are dried (magnesium sulfate), filtered, and evaporated to give (6-chloropyrazin-2-yl)[(4-methoxyphenyl) methyl]amine (35.5 g), a white solid.

Workup

  1. temperaturecooled
  2. customThe white solid is removed by filtration
  3. customthe filtrate evaporated
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washwashed successively with 2 M sodium hydroxide, water and aqueous sodium chloride
  6. dry with materialThe organics are dried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-a14c580565c34758a62d8f3e467e75c0
Source dataset
uspto-grants-2006_02
Patent number
US06995161B2

Reaction notes

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