Sodium Iodide → 4-(4-(4-(4-(3-Trifluoromethylphenyl)piperazinyl)butyl)-phenyl)-2-aminothiazole

HRID 329405Notes

Reaction equation

HRID 329405 reaction equation
Br.Cl[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([NH2:18])[S:16][CH:17]=2)=[CH:9][CH:8]=1.Cl.[F:20][C:21]([F:35])([F:34])[C:22]1[CH:23]=[C:24]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:25]=[CH:26][CH:27]=1.C(N(C(C)C)CC)(C)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CC(CC(C)C)=O>[F:35][C:21]([F:20])([F:34])[C:22]1[CH:23]=[C:24]([N:28]2[CH2:33][CH2:32][N:31]([CH2:3][CH2:4][CH2:5][CH2:6][C:7]3[CH:12]=[CH:11][C:10]([C:13]4[N:14]=[C:15]([NH2:18])[S:16][CH:17]=4)=[CH:9][CH:8]=3)[CH2:30][CH2:29]2)[CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 3084246TFMPP hydrochlorideHCID 142114294-(4-(4-Chlorobutyl)phenyl)-2-aminothiazole hydrobromide

Product 1

HCID 142114304-(4-(4-(4-(3-Trifluoromethylphenyl)piperazinyl)butyl)-phenyl)-2-aminothiazole

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a 125 ml round-bottomed flask equipped with condenser and N2 inlet were added 2.61 g (7.5 mmol) of 4-(4-(4-chlorobutyl)phenyl)-2-aminothiazole hydrobromide, 2.0 g (7.5 mmol) of N-(3-trifluoromethylphenyl)piperazine hydrochloride, 2.62 ml (15.0 mmol) of diisopropylethylamine, 1.59 g (15.0 mmol) of sodium carbonate, 5 mg of sodium iodide, and 50 ml of methylisobutylketone. The reaction was heated at reflux for 3.5 days, cooled, and the precipitate filtered, and the filtrate evaporated. The residue was chromatographed on silica gel using methylene chloride/ethyl acetate and ethyl acetate as eluents. The product fractions were concentrated, taken up in methylene chloride/methanol, precipitated by addition of ethyl acetate saturated with hydrochloride, evaporated, and the residue triturated with ether/ethyl acetate to afford a white solid, m.p. 174°-179° C., 0.87 g (23%).

Workup

  1. customTo a 125 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 3.5 days
  4. temperaturecooled
  5. filtrationthe precipitate filtered
  6. customthe filtrate evaporated
  7. customThe residue was chromatographed on silica gel
  8. concentrationThe product fractions were concentrated
  9. customprecipitated by addition of ethyl acetate saturated with hydrochloride
  10. customevaporated
  11. customthe residue triturated with ether/ethyl acetate
  12. customto afford a white solid, m.p. 174°-179° C., 0.87 g (23%)

Sources & evidence

ORD record
ord-b0d66922660d400b8d55e72f93b0914f
Source dataset
uspto-grants-1990_01
Patent number
US04891375

Reaction notes

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