Acetonitrile → HCID 9949431, compound

HRID 1289087Notes

Reaction equation

HRID 1289087 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:9][CH2:10][CH2:11]Cl)=[CH:4][CH:3]=1.C(#N)C.C(=O)([O-])[O-].[K+].[K+].[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>CCOCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:9][CH2:10][CH2:11][N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 107793021-[Bis(4-fluorophenyl)methoxy]-2-chloroethane

Product 1

HCID 9949431HCID 9949431, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-[Bis(4-fluorophenyl)methoxy]-2-chloroethane (3) (1.03 g, 3.6 mmol) was added to a flask containing acetonitrile (70 ml) and potassium carbonate (1.54 g, 11.1 mmol). This was followed by addition of piperidine (0.69 g, 8.1 mmol). The resulting mixture was heated to reflux for 48 hours under an atmosphere of nitrogen. At the end of this time, the solution was added to ether (75 ml), washed with water (100 ml) followed by brine (100 ml). The solution was then dried over magnesium sulfate, filtered and the solvents were evaporated under reduced pressure. The resulting clear yellow oil was then chromatographed on silica gel and eluted with 3:1 ethyl acetate/methanol to afford the desired product (5) (315 mg, 26.1%) as a clear and colorless oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 48 hours under an atmosphere of nitrogen
  3. washwashed with water (100 ml)
  4. dry with materialThe solution was then dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvents were evaporated under reduced pressure
  7. customThe resulting clear yellow oil was then chromatographed on silica gel
  8. washeluted with 3:1 ethyl acetate/methanol

Sources & evidence

ORD record
ord-87322c65c2164b0bb4ef8a1c9f8c0066
Source dataset
uspto-grants-1998_05
Patent number
US05747523

Reaction notes

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