Potassium Carbonate → HCID 68308576, compound

HRID 1021264Notes

Reaction equation

HRID 1021264 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=O)=O.[NH:19]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[N:19]1[CH:20]=[CH:21][C:22]([CH:25]2[CH2:30][CH2:29][N:28]([CH2:6][CH2:7][C:8]3[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=3)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:27][CH2:26]2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11395974-(4-Piperidyl)pyridineHCID 86686226HCID 86686226, compound

Product 1

HCID 68308576HCID 68308576, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 3-{2-[(methylsulfonyl)oxy]ethyl}benzoate (170 mg) was mixed with MeCN (3.4 ml), and 1,2,3,4,5,6-hexahydro-[4,4′]bipyridinyl (122 mg) and potassium carbonate (173 mg) were added thereto, followed by stirring at 60° C. overnight. After cooling to room temperature, the insoluble matter was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (MeOH/CHCl3) to obtain ethyl 3-{2-[4-(pyridin-4-yl)piperidin-1-yl]ethyl}benzoate (121 mg).

Workup

  1. additionwere added
  2. temperatureAfter cooling to room temperature
  3. customthe insoluble matter was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (MeOH/CHCl3)

Sources & evidence

ORD record
ord-1d89ea5620a5420281550aee5a6933c7
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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