Tetrahydrofuran → HCID 21939820, compound

HRID 1242914Notes

Reaction equation

HRID 1242914 reaction equation
[C:1]([O:8]C([O-])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=O.O1CCCC1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([CH:26]2[CH2:31][CH2:30][CH2:29][NH:28][CH2:27]2)=[O:25])=[CH:20][CH:19]=1>C(OCC)(=O)C>[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]([CH:26]2[CH2:31][CH2:30][CH2:29][N:28]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:8])[CH2:27]2)=[O:25])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21939878HCID 21939878, compoundHCID 22064466Tert-butyldicarbonate

Product 1

HCID 21939820HCID 21939820, compoundYield 111.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

t-Butyl dicarbonate (0.562 ml, 2.45 mmol) was added to a tetrahydrofuran solution (12 ml) of (4-aminophenyl)(3-piperidinyl)methanone (500 mg, 2.45 mmol) obtained in 1) under ice-cooling, which was stirred for 1.5 hours. Ethyl acetate was added to the reaction mixture, which was washed with saturated sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. The resulting oily substance was purified by silica gel column chromatography (development solvent; hexane:ethyl acetate=1:1), to give the titled compound (831 mg).

Workup

  1. customobtained in 1) under ice-
  2. temperaturecooling
  3. washwas washed with saturated sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled out under reduced pressure
  6. customThe resulting oily substance was purified by silica gel column chromatography (development solvent; hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-33d4f3d4dc8940a89660ad27d4e1cf20
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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