Potassium Carbonate → HCID 178448109, compound

HRID 478668Notes

Reaction equation

HRID 478668 reaction equation
Cl.[CH3:2][CH2:3][CH2:4][C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH2:11])[CH2:7][CH2:6]1.C(=O)([O-])[O-].[K+].[K+].[I-].C([N+]1(C)[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]1)C>C(O)C.O>[CH3:2][CH2:3][CH2:4][C@@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]2)[CH2:7][CH2:6]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 110975681-Ethyl-1-methyl-4-oxopiperidin-1-ium iodideHCID 178448121HCID 178448121, compound

Product 1

HCID 178448109HCID 178448109, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

cis-4-(2-methyl-ethyl)-cyclohexyl-amine hydrochloride(60.7 g) was dissolved in ethanol (725 ml). Potassium carbonate (51.8 g) and 1-ethyl-1-methyl-4-oxo-piperidinium iodide (126.6 g) dissolved in water (240 ml) were added and the mixture was refluxed for 1 hour. The reaction mixture was concentrated and extracted three times with dichloromethane. The combined organic layers were washed with aqueous bicarbonate and water, dried (MgSO4) and evaporated. Filtration over silica gel (cyclohexane/ethylacetate 17:3) yielded 69.7 g of a yellow oil which was distilled to yield the title compound (75%) as a slightly yellow oil. b.p. 111° C./0.45 mbar; m/z=223 [M+.].

Workup

  1. additionwere added
  2. temperaturethe mixture was refluxed for 1 hour
  3. concentrationThe reaction mixture was concentrated
  4. extractionextracted three times with dichloromethane
  5. washThe combined organic layers were washed with aqueous bicarbonate and water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. filtrationFiltration over silica gel (cyclohexane/ethylacetate 17:3)

Sources & evidence

ORD record
ord-f458364d80064c88bff48e2eb71d8552
Source dataset
uspto-grants-2003_11
Patent number
US06642247B2

Reaction notes

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