4-Methoxybenzylamine → HCID 22248994, compound

HRID 1270327Notes

Reaction equation

HRID 1270327 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 2M 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 2M 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-2c95a7166d01430f93ec770346568ede
Source dataset
uspto-grants-2007_04
Patent number
US07202250B2

Reaction notes

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