4-Methoxybenzylamine → HCID 22248994, compound

HRID 349180Notes

Reaction equation

HRID 349180 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[Cl:11][C:12]1[CH:17]=[N:16][CH:15]=[C:14](Cl)[N:13]=1>C(O)C>[Cl:11][C:12]1[N:13]=[C:14]([NH:8][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:15]=[N:16][CH:17]=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

Procedure

4-methoxybenzylamine (68.6 g, 0.5 mol) is added to a stirred solution of 2,6-dichloropyrazine (25 g, 0.167 mol) and ethanol (120 mL) in a sealed tube. The mixture is heated to 115 C for 12 hours 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. temperatureThe mixture is heated to 115 C for 12 hours
  2. temperaturecooled
  3. customThe white solid is removed by filtration
  4. customthe filtrate evaporated
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washwashed successively with 2M sodium hydroxide, water and aqueous sodium chloride
  7. dry with materialThe organics are dried (magnesium sulfate)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-446ddd3773f6456f89eab3461aeb069b
Source dataset
uspto-grants-2007_02
Patent number
US07179807B2

Reaction notes

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