Bromide ion → HCID 14856171, compound

HRID 846424Notes

Reaction equation

HRID 846424 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:8][CH2:7]1.[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.[C:34]([O-:37])([O-:36])=O.[K+].[K+].[Na+].[I-].[Br-].CC[O:45][C:46](C)=[O:47]>CO.CCOC(C)=O.CC#N>[C:46]([OH:47])(=[O:45])[C:34]([OH:37])=[O:36].[C:12]1([CH:9]2[S:8][CH2:7][N:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:29]3[CH2:28][CH2:27][N:26]([C:22]4[CH:23]=[CH:24][CH:25]=[C:20]([C:19]([F:32])([F:33])[F:18])[CH:21]=4)[CH2:31][CH2:30]3)[C:10]2=[O:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

9

Reactant 6

HCID 259Bromide ionHCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 14856127HCID 14856127, compound

Product 1

HCID 14856171HCID 14856171, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 3-(4-bromobutyl)-5-phenyl-4-thiazolidinone (4.67 g), 1-(3-trifluoromethylphenyl)piperazine (3.76 g), K2CO3 (5.15 g), NaI (300 mg) and CH3CN (150 mL) was heated at reflux (bath temperature 95° C.) under N2. After 17 hours, TLC analysis (silica gel, 5% MeOH/EtOAc) showed the absence of starting bromide and presence of one major product with an Rf =0.33. The mixture was cooled to room temperature, EtOAc (100 mL) was added, and the mixture filtered. The filtrate was concentrated in vacuo to an oil which was triturated with EtOAc. The mixture was filtered and the filtrate concentrated again in vacuo to 7.59 g of an oil. The crude product was chromatographed (Waters Prep 500, 2 columns, silica gel, 5% MeOH/EtOAc) to give 6.42 g of an oil, and from this 4.47 g of the oxalate salt of this amine was prepared. The solid was recrystallized from EtOH/EtOAc giving 3.65 g of fine white crystals, mp 140°-142° C.

Workup

  1. temperaturewas heated
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationthe mixture filtered
  4. concentrationThe filtrate was concentrated in vacuo to an oil which
  5. customwas triturated with EtOAc
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate concentrated again in vacuo to 7.59 g of an oil
  8. customThe crude product was chromatographed (Waters Prep 500, 2 columns, silica gel, 5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-b16b2f83ed0c4e8583b40771b761dbb5
Source dataset
uspto-grants-1992_08
Patent number
US05136037

Reaction notes

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