Potassium Carbonate → HCID 66633388, compound

HRID 1961429Notes

Reaction equation

HRID 1961429 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH3:10][C@H:11]1[CH2:16][O:15][CH2:14][CH2:13][NH:12]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O>[CH3:10][C@@H:11]1[N:12]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:13][CH2:14][O:15][CH2:16]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 12012220(3S)-3-methylmorpholine

Product 1

HCID 66633388HCID 66633388, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

4-Fluorobenzonitrile (359 mg, 2.97 mmol), (S)-3-methylmorpholine (150 mg, 1.48 mmol) and K2CO3 were suspended in DMSO (1.5 ml). The mixture was stirred for 70 hours at 110° C. in a closed high-pressure flask. The reaction was cooled, diluted with water (50 ml) and extracted with EtOAc (3*20 ml). Combined organics were washed with water (20 ml), dried over MgSO4 and evaporated. The product was purified by flash chromatography using pet.ether/EtOAc (3:1) as eluent to give 130 mg (43%) of the title compound as pale solids.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with EtOAc (3*20 ml)
  3. washCombined organics were washed with water (20 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-ccbe5b865c1640edab05bc330c8e2704
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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