Ethylenediamine → 2-[(4,5-Dihydro-1H-imidazol-2-yl)phenylmethyl]pyridine

HRID 1580306Notes

Reaction equation

HRID 1580306 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:14]#[N:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:16](N)[CH2:17][NH2:18].[S]>>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:14]1[NH:18][CH2:17][CH2:16][N:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 95510alpha-Phenyl-2-pyridineacetonitrileHCID 5362487Sulfur

Product 1

HCID 537623412-[(4,5-Dihydro-1H-imidazol-2-yl)phenylmethyl]pyridine

Conditions

Temperature
125 °C

Procedure

Under a nitrogen atmosphere, carefully reflux (bath temperature of 125° C) a mixture containing 19.4 g. of 2-pyridylbenzyl cyanide, 6.6 g. of ethylene diamine and 0.2 g. of sulphur for 5 hrs. Cool the reaction mixture and under a nitrogen atmosphere dissolve the residue in 300 ml. of benzene, and water wash, dry (over anhydrous potassium carbonate) and filter the benzene solution. Concentrate the filtrate to a small volume whereupon the product crystallizes. Filter the crystals to yield 2-[α-(2-pyridyl) benzyl]-imidazoline, m.p. 134°-136° C. The maleate salt, m.p. 132°-135°C, is prepared from maleic acid and is crystallized from isopropanol.

Workup

  1. additioncontaining 19.4 g
  2. temperatureCool the reaction mixture
  3. dissolutionunder a nitrogen atmosphere dissolve the residue in 300 ml
  4. washof benzene, and water wash
  5. dry with materialdry (over anhydrous potassium carbonate)
  6. filtrationfilter the benzene solution
  7. concentrationConcentrate the filtrate to a small volume whereupon the product
  8. customcrystallizes
  9. filtrationFilter the crystals

Sources & evidence

ORD record
ord-a779ce8c90574c7b9aeeb6493f8c37c4
Source dataset
uspto-grants-1976_01
Patent number
US03932431

Reaction notes

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