Piperidine → HCID 54102600, compound

HRID 2399616Notes

Reaction equation

HRID 2399616 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH3:15])[CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[C:9]=1[CH2:10]O)([O-:3])=[O:2].C[Si](C)(C)N[Si](C)(C)C.[CH:25](=O)[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1.N1CCCCC1.C(OCCCC)(=[O:43])C>>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:15][OH:43])[CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[C:9]=1[CH:10]=[CH:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)([O-:3])=[O:2]

Participants

6

Reactant 5

HCID 8082PiperidineHCID 13838HexamethyldisilazaneHCID 312444-MethoxybenzaldehydeHCID 31272Butyl AcetateHCID 18991137HCID 18991137, compound

Product 1

HCID 54102600HCID 54102600, compound

Procedure

A solution of 2,6-dinitro-4-hydroxymethyltoluene (9) from Example 7 (3 grams ) and hexamethyldisilazane (2.28 grams) in n-butyl acetate (20 grams) was combined with p-anisaldehyde (1.92 grams) and piperidine (0.384 gram) and the mixture was heated to reflux under a N2 blanket for 14 hours The reaction was cooled, concentrated in vacuo and the crude product analyzed by 1H NMR to reveal the characteristic AB splitting pattern of the stilbene protons. The product was confirmed by comparison to an authentic sample prepared according to Example 9 using thin layer chromatography and NMR techniques, confirming the presence of structure (10) ##STR10##

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux under a N2 blanket for 14 hours The reaction
  3. temperaturewas cooled
  4. concentrationconcentrated in vacuo
  5. customprepared

Sources & evidence

ORD record
ord-e28d4b392c1c42e48e69ca746aef8820
Source dataset
uspto-grants-1995_09
Patent number
US05449834

Reaction notes

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