Potassium Carbonate → HCID 54120181, compound

HRID 1066987Notes

Reaction equation

HRID 1066987 reaction equation
[C:1]1([C:7]2([C:13]3[O:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](C(N)CCBr)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[C:21]([O:20][C:18](=[O:19])[NH:10][CH2:9][CH2:8][CH2:7][N:10]1[CH2:9][CH2:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)([CH3:22])([CH3:23])[CH3:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 14193053HCID 14193053, compoundHCID 22993562HCID 22993562, compound

Product 1

HCID 54120181HCID 54120181, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-phenyl-4-furan-2-yl-piperidine and 3-Boc-aminopropylbromide (0.30 g, 1.3 mmol) with 0.5 g of K2CO3 in 20 ml of dioxane was stirred at reflux for 12 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic solution was dried over Na2SO4 and concentrated in vacuo to yield an oil which was subjected to column chromatography over silica gel (EtOAc) to provide 0.21 g (0.54 mmol, 32% for two steps) of 3-(4-phenyl-4-(furan-2-yl)piperidin-1-yl)propylcarbamic acid tert-butyl ester as a colorless oil. The ester in 5 ml of CH2Cl2 was added with 1 ml of CF3CO2H and resulting solution was stirred for 1 h at 25° C. The reaction mixture was concentrated in vacuo to yield oily mixture, which was dissolved in EtOAc and washed with aqueous NaHCO3. Concentration of the reaction mixture provided the desired product as an oil (0.13 g, 0.45 mmol, 84%).

Workup

  1. temperatureat reflux for 12 h
  2. extractionextracted with EtOAc
  3. dry with materialThe organic solution was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto yield an oil which

Sources & evidence

ORD record
ord-ef337889f0684cebad8781e58028ff56
Source dataset
uspto-grants-2001_06
Patent number
US06245773B1

Reaction notes

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