2-Vinylpyridine → HCID 19088490, compound

HRID 1463869Notes

Reaction equation

HRID 1463869 reaction equation
[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:11][CH2:12][CH2:13][NH:14][CH3:15])[C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)=[CH2:23]>O1CCOCC1>[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:11][CH2:12][CH2:13][N:14]([CH3:15])[CH2:23][CH2:22][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[C:8]([NH2:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 75212-VinylpyridineHCID 190884752,2-Diphenyl-5-methylaminopentanamide

Product 1

HCID 19088490HCID 19088490, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution containing 2,2-diphenyl-5-methylaminopentanamide (2.0 g--see Preparation 3) and 2-vinylpyridin (1.1 ml) in dioxan (15 ml) was heated under reflux for 48 hours. The mixture was concentrated in vacuo and the residue partitioned between dichloromethane (50 ml) and water (50 ml). The dichloromethane layer was dried (MgSO4) and concentrated in vacuo to give a solid which was purified by column chromatography eluting with hexane containing dichloromethane (50% up to 100%) and then with dichloromethane containing methanol (0% up to 5%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as an oil which was crystallised from acetonitrile, yield 0.5 g, m.p. 134°-136°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue partitioned between dichloromethane (50 ml) and water (50 ml)
  5. dry with materialThe dichloromethane layer was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give a solid which
  8. customwas purified by column chromatography
  9. washeluting with hexane
  10. additioncontaining dichloromethane (50% up to 100%)
  11. additionwith dichloromethane containing methanol (0% up to 5%)
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-246655f03e724fbc9014552f1a96581f
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

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