Sodium Carbonate → 1-[4-Fluorobenzoyl]-4-[4-(7-trifluoromethyl-4-quinolinylamino)benzenesulphonyl]piperazine

HRID 568895Notes

Reaction equation

HRID 568895 reaction equation
Cl.[F:2][C:3]([F:26])([F:25])[C:4]1[CH:13]=[C:12]2[C:7]([C:8]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=3)=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1.Cl.[F:28][C:29]1[CH:42]=[CH:41][C:32]([C:33]([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[O:34])=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl.O>[F:28][C:29]1[CH:42]=[CH:41][C:32]([C:33]([N:35]2[CH2:40][CH2:39][N:38]([S:21]([C:18]3[CH:19]=[CH:20][C:15]([NH:14][C:8]4[C:7]5[C:12](=[CH:13][C:4]([C:3]([F:26])([F:25])[F:2])=[CH:5][CH:6]=5)[N:11]=[CH:10][CH:9]=4)=[CH:16][CH:17]=3)(=[O:23])=[O:22])[CH2:37][CH2:36]2)=[O:34])=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 201495894-(7-Trifluoromethyl-4-quinolinylamino)benzenesulphonyl chloride hydrochlorideHCID 20149590(4-Fluorophenyl)(piperazin-1-yl)methanone hydrochloride

Product 1

HCID 136082991-[4-Fluorobenzoyl]-4-[4-(7-trifluoromethyl-4-quinolinylamino)benzenesulphonyl]piperazineYield 20.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

4-(7-Trifluoromethyl-4-quinolinylamino)benzenesulphonyl chloride hydrochloride (3.5 g, 0.008 mol) was added portionwise to a cold (10°), well stirred mixture of 1-(4-fluorobenzoyl)piperazine hydrochloride (2.0 g, 0.008 mol) in chloroform (50 ml) and sodium carbonate (10.0 g) in water (50 ml). The cooling bath was removed and the mixture was allowed to warm to room temperature. After half an hour, the mixture was filtered and the filtrate separated. The chloroform layer was dried (MgSO4). The solvent was removed by evaporation to give a yellow gum. The gum was crystallised from ethanol-water, then purified by column chromatography (basic Al2O3-chloroform) followed by recrystallisation from ethanol, to give the pure title compound (0.9 g), m.p. 172°-174.5° C.

Workup

  1. customThe cooling bath was removed
  2. waitAfter half an hour
  3. filtrationthe mixture was filtered
  4. customthe filtrate separated
  5. dry with materialThe chloroform layer was dried (MgSO4)
  6. customThe solvent was removed by evaporation
  7. customto give a yellow gum
  8. customThe gum was crystallised from ethanol-water
  9. custompurified by column chromatography (basic Al2O3-chloroform)
  10. customfollowed by recrystallisation from ethanol

Sources & evidence

ORD record
ord-439b1e38510643638113b311ff7c06d9
Source dataset
uspto-grants-1988_03
Patent number
US04730047

Reaction notes

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