Potassium Carbonate → HCID 68690147, compound

HRID 2245336Notes

Reaction equation

HRID 2245336 reaction equation
[I-].C([N+]1(C)[CH2:14][CH2:13][C:12](=[O:15])[CH:11]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:10]1)C1C=CC=CC=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[NH2:26].C(=O)([O-])[O-].[K+].[K+]>O.C(O)C>[CH2:16]([CH:11]1[C:12](=[O:15])[CH2:13][CH2:14][N:26]([C:25]2[CH:27]=[C:28]([O:32][CH3:33])[C:29]([O:30][CH3:31])=[C:23]([O:22][CH3:21])[CH:24]=2)[CH2:10]1)[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 322853,4,5-TrimethoxyanilineHCID 86605588HCID 86605588, compound

Product 1

HCID 68690147HCID 68690147, compoundYield 204.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A slurry of 1-benzyl-3-butyl-1-methyl-4-oxo-piperidinium iodide (306 mg) in water (2 ml) was added in one portion to a refluxing solution of 3,4,5-trimethoxy aniline (929 mg) and anhydrous potassium carbonate (33 mg) in ethanol (4 ml). The dark solution was heated to reflux for three hours. Water was added and the reaction was extracted twice with DCM. The combined organic layers were dried over sodium sulfate, filtered and the solvent was evaporated to leave a dark oil, which was purified by flash chromatography (ethyl acetate/hexanes 1:1) to give the product as a colorless oil (520 mg). MS (ESI): 322.4 (MH+).

Workup

  1. temperatureThe dark solution was heated
  2. temperatureto reflux for three hours
  3. extractionthe reaction was extracted twice with DCM
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customto leave a dark oil, which
  8. customwas purified by flash chromatography (ethyl acetate/hexanes 1:1)

Sources & evidence

ORD record
ord-4d9791eba0f34d24ae92b2388f259968
Source dataset
uspto-grants-2010_03
Patent number
US07683079B2

Reaction notes

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