Piperidine → HCID 53925198, compound

HRID 2399615Notes

Reaction equation

HRID 2399615 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 once 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 once 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-c74a59c6ec1d4821b2739dccfda90498
Source dataset
uspto-grants-1995_09
Patent number
US05449834

Reaction notes

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