Phenethylamine → HCID 44554831, compound

HRID 220007Notes

Reaction equation

HRID 220007 reaction equation
Cl[C:2]1[CH:7]=[N+:6]([O-:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[CH2:10]([NH2:18])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O>[Cl:9][C:4]1[N:3]=[C:2]([NH:18][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[N+:6]([O-:8])[CH:5]=1

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 3824405HCID 3824405, compound

Product 1

HCID 44554831HCID 44554831, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 0.330 g (2.0 mmol) of 2,6-dichloro-pyrazine 4-oxide in 0.485 g (4.0 mmol) of phenethylamine was allowed to stir under reflux for 10 min. pCooled water was added and the mixture extracted with dichloromethane, dried over sodium sulfate and evaporated to dryness. pThe residue obtained was purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol/diethylamine in the proportions 97/3/0.3 to give after trituration with diethyl ether 0.370 g (74%) of pure product as a grey solid.

Workup

  1. temperatureunder reflux for 10 min.
  2. additionwas added
  3. extractionthe mixture extracted with dichloromethane
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. custompThe residue obtained
  7. customwas purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol/diethylamine in the proportions 97/3/0.3
  8. customto give after trituration with diethyl ether 0.370 g (74%) of pure product as a grey solid

Sources & evidence

ORD record
ord-b562314a905b4f3aa6223f53683cd32c
Source dataset
uspto-grants-2012_06
Patent number
US08202874B2

Reaction notes

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