Hydrochloric Acid → 4-(4-(2-(4-(3-Trifluoromethylphenyl)piperazinyl)ethyl)phenyl)-2-amino-5-methylthiazole

HRID 329396Notes

Reaction equation

HRID 329396 reaction equation
Br.Cl[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([NH2:16])[S:14][CH:15]=2)=[CH:7][CH:6]=1.Cl.[F:18][C:19]([F:33])([F:32])[C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1.[CH2:34](N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].Cl>C(OCC)(=O)C.O.C(OCC)(=O)C.CO.CCOCC.C(O)C>[F:33][C:19]([F:18])([F:32])[C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][N:29]([CH2:3][CH2:4][C:5]3[CH:10]=[CH:9][C:8]([C:11]4[N:12]=[C:13]([NH2:16])[S:14][C:15]=4[CH3:34])=[CH:7][CH:6]=3)[CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 3084246TFMPP hydrochlorideHCID 147269834-(2-Chloroethyl)phenyl-2-aminothiazole hydrobromide

Product 1

HCID 147269984-(4-(2-(4-(3-Trifluoromethylphenyl)piperazinyl)ethyl)phenyl)-2-amino-5-methylthiazole

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 21584119Ethylacetate methanolSolventHCID 22728543Water ethylacetateSolvent

Procedure

To a 35 ml round-bottomed flask equipped with condenser and N2 inlet were added 0.75 g (2.59 mmol) of 4-(4-(2-chloroethyl)phenyl)-2-aminothiazole hydrobromide, 0.69 g (2.59 mmol) of N-(3-trifluoromethylphenyl)piperazine hydrochloride, 1.08 ml (7.78 mmol) of triethylamine, 0.27 g (2.59 mmol) of sodium carbonate, 5 mg of sodium iodide, and 9.5 ml of ethanol. The reaction was heated at reflux, cooled, and taken up in ethyl acetate/water. The layers were separated, the ethyl acetate washed with brine, dried, and evaporated to give an oil. The oil was chromatographed on silica gel using ethyl acetate as eluent to give an oil. The oil was taken up in ethyl acetate/methanol, ether saturated with HCl was added, the precipitate filtered, washed with ether, and dried to give a white solid, 0.72 g (50%), m.p. 110°-115° C.

Workup

  1. customTo a 35 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was heated
  3. temperatureat reflux
  4. temperaturecooled
  5. customThe layers were separated
  6. washthe ethyl acetate washed with brine
  7. customdried
  8. customevaporated
  9. customto give an oil
  10. customThe oil was chromatographed on silica gel
  11. customto give an oil
  12. filtrationthe precipitate filtered
  13. washwashed with ether
  14. customdried
  15. customto give a white solid, 0.72 g (50%), m.p. 110°-115° C.

Sources & evidence

ORD record
ord-496521a9e8c74e6dad62f6677c2deacd
Source dataset
uspto-grants-1990_01
Patent number
US04891375

Reaction notes

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