Piperidine → HCID 66990853, compound

HRID 454677Notes

Reaction equation

HRID 454677 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[CH2:47]([O:54][C:55]1[CH:81]=[CH:80][C:79](Br)=[CH:78][C:56]=1[C:57]([NH:59][C:60]1[CH:69]=[C:68]([C:70]2[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=2)[C:67]([O:76][CH3:77])=[CH:66][C:61]=1[C:62]([O:64][CH3:65])=[O:63])=[O:58])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH2:47]([O:54][C:55]1[CH:81]=[CH:80][C:79]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:78][C:56]=1[C:57]([NH:59][C:60]1[CH:69]=[C:68]([C:70]2[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=2)[C:67]([O:76][CH3:77])=[CH:66][C:61]=1[C:62]([O:64][CH3:65])=[O:63])=[O:58])[C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1

Participants

10

Reactant 4

HCID 8082PiperidineHCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 66990107HCID 66990107, compound

Product 1

HCID 66990853HCID 66990853, compound

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Piperidine (0.012 mL), cesium carbonate (0.054 g), tris(dibenzylideneacetone)dipalladium(0) (2.3 mg), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (5.9 mg), and palladium(II) acetate (1.1 mg) were added to a toluene (2.0 mL) solution of methyl 2-(2-(benzyloxy)-5-bromobenzamido)-5-methoxy-4-phenylbenzoate (0.045 g), followed by heating to reflux under a nitrogen atmosphere for 2 hours and 20 minutes. The reaction mixture was cooled to room temperature, and ethyl acetate and water were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate] to obtain 0.034 g of methyl 2-(2-(benzyloxy)-5-(piperidin-1-yl)benzamido)-5-methoxy-4-phenylbenzoate as a yellow solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 2 hours and 20 minutes
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-c859ce6675b44fb9b585495ff0aa1d9e
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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