Potassium Carbonate → HCID 60196778, compound

HRID 1523406Notes

Reaction equation

HRID 1523406 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.Cl[CH2:20][C:21]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:13]=[CH:14][C:15]([NH:16][CH2:20][C:21]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[O:22])=[CH:17][CH:18]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74040Morpholine, 4-(chloroacetyl)-HCID 23151271HCID 23151271, compound

Product 1

HCID 60196778HCID 60196778, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(1-Cyclobutyl piperidin-4-yloxy)aniline (0.5 g, 0.002 moles), 2-Chloro-1-(morpholin-4-yl)ethanone (0.5 g, 0.003) and potassium carbonate (0.56 g, 0.004 moles) in dimethylformamide (25 ml) was stirred at reflux temperature. After completion of reaction, the mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (250 mL) and water (250 mL). The combined organic layers were washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure. The crude compound was purified by flash chromatography (chloroform: triethylamine, 9.5:0.5) to obtain the title compound 0.3 g (Yield: 40%).

Workup

  1. temperatureat reflux temperature
  2. customAfter completion of reaction
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customthe residue was partitioned between ethyl acetate (250 mL) and water (250 mL)
  5. washThe combined organic layers were washed with brine solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude compound was purified by flash chromatography (chloroform: triethylamine, 9.5:0.5)

Sources & evidence

ORD record
ord-cd43f8e3494340f8865d521e2ed63bd0
Source dataset
uspto-grants-2015_07
Patent number
US09079888B2

Reaction notes

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