Phenethylamine → Pyridine, 4-(phenethylamino)-

HRID 235053Notes

Reaction equation

HRID 235053 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH2:8]([NH2:16])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[NH4+]>O>[C:10]1([CH2:9][CH2:8][NH:16][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 122884-ChloropyridineHCID 14923Ammonium Hydroxide

Product 1

HCID 204216Pyridine, 4-(phenethylamino)-Yield 16%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture composed of 2.0 g (0.0176 m) of 4-chloropyridine and 4.3 g (0.0352 m) of phenethylamine was heated under nitrogen to 160°-165° C for one hour. The mixture was then cooled and 200 mL of a 50/50 mixture of ammonium hydroxide in water was added. The product was extracted into CH2Cl2, which was then concentrated to dryness. The resulting material was purified by HPLC on silica gel, eluting with ethyl acetate to provide 0.560 g of the title product.

Workup

  1. temperaturewas heated under nitrogen to 160°-165° C for one hour
  2. temperatureThe mixture was then cooled
  3. additionwas added
  4. extractionThe product was extracted into CH2Cl2, which
  5. concentrationwas then concentrated to dryness
  6. customThe resulting material was purified by HPLC on silica gel
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-af80aacf27e84d3aa57a99f7509102ae
Source dataset
uspto-grants-1997_01
Patent number
US05597836

Reaction notes

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