Water → 1-(3,4-Dimethoxy-phenyl)-piperidine-4-one

HRID 2245344Notes

Reaction equation

HRID 2245344 reaction equation
[I-].C([N+]1(C)[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)C1C=CC=CC=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[NH2:22].C(=O)([O-])[O-].[K+].[K+].O>C(O)C.C(=O)([O-])[O-].[K+].[K+]>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([N:22]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)[CH:23]=[CH:24][C:25]=1[O:26][CH3:27]

Participants

7

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 227703,4-DimethoxyanilineHCID 110780641-Benzyl-1-methyl-4-oxopiperidinium iodide

Product 1

HCID 220002541-(3,4-Dimethoxy-phenyl)-piperidine-4-oneYield 61.8%

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A slurry of 1-benzyl-1-methyl-4-oxo-piperidinium iodide (9270 mg), 3,4-dimethoxy aniline (3900 mg) and anhydrous potassium carbonate (437 mg) in ethanol (90 ml)/water (45 ml) were heated to reflux for 6 hours. Additional potassium carbonate (200 mg) was added and the reaction was heated to 100° C. over night. Water (50 ml) was added to the reaction mixture, which was extracted three times with DCM. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and the solvent was evaporated in vacuo to leave the crude product as a dark oil. The residue was purified by column chromatography (ethyl acetate/hexanes=1:1) to yield the product as a yellow solid (3700 mg). MS (ESI): 236.1 (MH+).

Workup

  1. temperatureto reflux for 6 hours
  2. extractionwas extracted three times with DCM
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated in vacuo
  7. customto leave the crude product as a dark oil
  8. customThe residue was purified by column chromatography (ethyl acetate/hexanes=1:1)

Sources & evidence

ORD record
ord-d742b2973ace485ca544ba4a79fd708c
Source dataset
uspto-grants-2010_03
Patent number
US07683079B2

Reaction notes

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