2-(4-Aminophenyl)ethylamine → HCID 21190160, compound

HRID 619530Notes

Reaction equation

HRID 619530 reaction equation
Cl[C:2]1[N:7]2[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([CH3:11])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][NH2:26])=[CH:20][CH:19]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][NH:26][C:2]2[N:7]3[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([CH3:11])[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 728952-(4-Aminophenyl)ethylamineHCID 81531DiisopropylethylamineHCID 2736382Ethyl 5-chloro-2-methylimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 21190160HCID 21190160, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4.07 g (17.1 mmol) of 5-chloro-3-ethoxycarbonyl-2-methylimidazo[1,2-a)pyridine, 3.48 g (25.6 mmol) of 2-(4-aminophenyl)ethylamine and 4.41 g (34.1 mmol) of N,N-diisopropylethylamine in 60 ml of acetonitrile was heated for 64 hours under reflux with stirring. After cooling, the solvent was distilled off. To the residue was added chloroform. The residue was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off. The residue was purified by column chromatography (eluent: chloroform/methanol=30:1) and recrystallized from ethyl acetate-n-hexane to give 4.37 g of the desired compound (75.7%, pale brown crystals).

Workup

  1. temperaturewas heated for 64 hours
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. distillationthe solvent was distilled off
  5. additionTo the residue was added chloroform
  6. washThe residue was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customThe residue was purified by column chromatography (eluent: chloroform/methanol=30:1)
  10. customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-824aa5e34e1840fab29a7b6aefcf2fcc
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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