Potassium Carbonate → HCID 178510061, compound

HRID 1047359Notes

Reaction equation

HRID 1047359 reaction equation
C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=1.[NH2:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23][CH2:22]1>O.C(#N)C>[OH:27][C@H:24]1[CH2:25][CH2:26][C@H:21]([NH:20][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)[CH2:22][CH2:23]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6050854-Fluoro-2-(trifluoromethyl)benzonitrileHCID 178511715HCID 178511715, compound

Product 1

HCID 178510061HCID 178510061, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (304 mg, 2.2 mmol) was dissolved in a minimum amount of water. Next, 4-fluoro-2-trifluoromethylbenzonitrile (378 mg, 2.0 mmol) and trans-4-aminocyclohexanol (460 mg, 4.0 mmol) dissolved in acetonitrile (10 mL) were added. The resulting mixture was then heated at 80° C. for 3 days. After cooling at room temperature, the mixture was concentrated under vacuum, taken up in ethyl acetate (15 mL), washed with saturated aqueous ammonium chloride (2×10 mL), and washed with water (10 mL). The organic phase was collected and dried over sodium sulfate, filtered, and concentrated under vacuum. The desired product was isolated as a colorless solid (456 mg, 80% yield).

Workup

  1. additionwere added
  2. temperatureAfter cooling at room temperature
  3. concentrationthe mixture was concentrated under vacuum
  4. washwashed with saturated aqueous ammonium chloride (2×10 mL)
  5. washwashed with water (10 mL)
  6. customThe organic phase was collected
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-72e93bb95ecd455591cf62f24ed77a5e
Source dataset
uspto-grants-2013_10
Patent number
US08569495B2

Reaction notes

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