Piperidine → HCID 53925198, compound

HRID 2395907Notes

Reaction equation

HRID 2395907 reaction equation
[N+:1]([C:4]1[C:9]([CH3:10])=[C:8]([N+:11]([O-:13])=[O:12])[CH:7]=C(C)[C:5]=1C([O-])=O)([O-:3])=[O:2].[CH:18](=O)[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1.N1CCCCC1.[C:34]([O:37][CH2:38]C)(=[O:36])[CH3:35]>>[N+:1]([C:4]1[CH:5]=[C:35]([C:34]([O:37][CH3:38])=[O:36])[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[CH:10]=[CH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 8082PiperidineHCID 8857Ethyl AcetateHCID 312444-MethoxybenzaldehydeHCID 86748976HCID 86748976, compound

Product 1

HCID 53925198HCID 53925198, compound

Procedure

A mixture of 3,5-dinitro-p-methyltoluate (120.08 grams) from Example 1, p-anisaldehyde (68.08 grams), activated basic alumina oxide (150 mesh, 58 angstrom, 70.00 grams), and ethyl acetate (150.0 grams) was heated to reflux. Piperidine (15.3 grams) was added dropwise over 5 hours and the reaction held at reflux for another 6.5 hours. Upon cooling, a yellow crystalline product precipitated and was isolated by filtration. The crude product was recrystallized one time from concentrated ethyl acetate to recover 77.6 grams of bright yellow 2,6-dinitro-4- carbomethoxy-4'-methoxystilbene (4). The product was characterized by NMR and had a melting point of 141.5° to 143° C.

Workup

  1. temperaturewas heated to reflux
  2. temperatureat reflux for another 6.5 hours
  3. temperatureUpon cooling
  4. customa yellow crystalline product precipitated
  5. customwas isolated by filtration
  6. customThe crude product was recrystallized one time from concentrated ethyl acetate
  7. customto recover 77.6 grams of bright yellow 2,6-dinitro-4- carbomethoxy-4'-methoxystilbene (4)

Sources & evidence

ORD record
ord-754c091472b146b9a2bc67e3ba4320af
Source dataset
uspto-grants-1996_02
Patent number
US05489714

Reaction notes

Loading…