Potassium Carbonate → HCID 68684773, compound

HRID 2245343Notes

Reaction equation

HRID 2245343 reaction equation
[I-].C([N+:9]1(C)[CH2:14][CH2:13][C:12](=[O:15])[CH:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[CH2:10]1)C1C=CC=CC=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:30]=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34])N.C(=O)([O-])[O-].[K+].[K+]>O.C(O)C>[C:17]1([CH3:22])[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH:11]1[C:12](=[O:15])[CH2:13][CH2:14][N:9]([C:28]2[CH:30]=[C:31]([O:35][CH3:36])[C:32]([O:33][CH3:34])=[C:26]([O:25][CH3:24])[CH:27]=2)[CH2:10]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 322853,4,5-TrimethoxyanilineHCID 86605591HCID 86605591, compound

Product 1

HCID 68684773HCID 68684773, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A slurry of 1-benzyl-1-methyl-4-oxo-3-o-tolyl-piperidinium iodide (1000 mg) in water (5 ml) was added in one portion to a refluxing solution of 3,4,5-trimethoxy aniline (395 mg) and anhydrous potassium carbonate (37 mg) in ethanol (10 ml). The reaction was heated to reflux over night. Water was added and the reaction was extracted four times with DCM. The combined organic layers were dried over sodium sulfate, filtered and the solvent was evaporated to leave a red-brown oil, which was purified by flash chromatography (diethyl ether) to give the product as a yellow oil (600 mg). MS (ESI): 356.2 (MH+).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux over night
  3. extractionthe reaction was extracted four times 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 red-brown oil, which
  8. customwas purified by flash chromatography (diethyl ether)

Sources & evidence

ORD record
ord-145e76dc515d4b349d6ca7776aad9697
Source dataset
uspto-grants-2010_03
Patent number
US07683079B2

Reaction notes

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