Trifluoroacetic acid → HCID 19897016, compound

HRID 1196979Notes

Reaction equation

HRID 1196979 reaction equation
Cl.[NH2:2][CH:3]([CH3:23])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:8][CH:7]=1)=O.[CH:24]1([N:30]=[C:31]=[O:32])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(N(CC)CC)C.FC(F)(F)C(O)=O>CC(C)=O>[CH:24]1([N:30]2[C:4]([C:6]3[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:8][CH:7]=3)=[C:3]([CH3:23])[NH:2][C:31]2=[O:32])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 18502Cyclohexyl isocyanateHCID 19897002HCID 19897002, compound

Product 1

HCID 19897016HCID 19897016, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Amino-4'-decyloxypropiophenone hydrochloride (500 mg, 1.46 mmol) was suspended in acetone (180 ml) under ice-cooling, and cyclohexyl isocyanate (201 mg, 1.61 mmol) was added thereto. Triethylamine (590 mg, 5.84 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 overnight at room temperature. The solvent was removed by evaporation in vacuo, and the residue was extracted with ethyl ether. The extract was washed successively with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. Evaporation of the solvent provided a crude product, which was then purified by column chromatography (chloroform/ethanol=50/1 (v/v)) to give the title compound. Yield: 235 mg (39%), m.p. 137°-138° C.

Workup

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

Sources & evidence

ORD record
ord-9b846025a8834694a1c13bc34c2793e3
Source dataset
uspto-grants-1992_05
Patent number
US05116858

Reaction notes

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