Trifluoroacetic acid → HCID 19897012, compound

HRID 1196976Notes

Reaction equation

HRID 1196976 reaction equation
Cl.[NH2:2][CH:3]([CH3:18])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1)=O.[CH:19]([N:22]=[C:23]=[O:24])([CH3:21])[CH3:20].C(N(CC)CC)C.FC(F)(F)C(O)=O>CC(C)=O>[CH:12]1([C:9]2[CH:10]=[CH:11][C:6]([C:4]3[N:22]([CH:19]([CH3:21])[CH3:20])[C:23](=[O:24])[NH:2][C:3]=3[CH3:18])=[CH:7][CH:8]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 19897006HCID 19897006, compound

Product 1

HCID 19897012HCID 19897012, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Amino-4'-cyclohexylpropiophenone hydrochloride (477 mg, 1.78 mmol) was suspended in acetone (30 ml) under ice-cooling, and isopropyl isocyanate (198 mg, 2.33 mmol) was added thereto. Triethylamine (533 mg, 5.28 mmol) was added, and the mixture was stirred for one hour under ice-cooling. After addition of trifluoroacetic acid (2 ml), the mixture was stirred for 2 days at room temperature. The solvent was removed by evaporation in vacuo, and the residue was extracted with dichloromethane. The extract was washed successively with water and saturated aqueous sodium chloride, and dried over magnesium sulfate. Evaporation of the solvent provided a crude product, which was purified by column chromatography (chloroform/ ethanol=50/1 (v/v)) and recrystalization (ethanol-chloroform) to give the title compound. Yield: 351 mg (66%), m.p. 274° C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for 2 days at room temperature
  4. customThe solvent was removed by evaporation in vacuo
  5. extractionthe residue was extracted with dichloromethane
  6. washThe extract was washed successively with water and saturated aqueous sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customEvaporation of the solvent
  9. customprovided a crude product, which
  10. customwas purified by column chromatography (chloroform/ ethanol=50/1 (v/v)) and recrystalization (ethanol-chloroform)

Sources & evidence

ORD record
ord-e2d27f9a068441ee95eac192c14d033f
Source dataset
uspto-grants-1992_05
Patent number
US05116858

Reaction notes

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