Bromide ion → 3-[4-[1-(2-Methylphenyl)-4-piperazinyl]butyl]5,5-dimethyl-4-thiazolidinone hydrochloride

HRID 1594797Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1594797
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]([CH3:13])([CH3:12])[S:8][CH2:7]1.[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[Br-].CO.C(Cl)[Cl:39]>C(OCC)(=O)C.C(#N)C>[ClH:39].[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][N:24]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[C:10](=[O:11])[C:9]([CH3:13])([CH3:12])[S:8][CH2:7]2)[CH2:23][CH2:22]1

Komponenten

9

Edukt 6

HCID 259Bromide ionHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 919652-MeppHCID 106117723-(4-Bromobutyl)-5,5-dimethyl-4-thiazolidinoneHCID 21226129Dichloromethane methanol

Produkt 1

HCID 148561473-[4-[1-(2-Methylphenyl)-4-piperazinyl]butyl]5,5-dimethyl-4-thiazolidinone hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of 3-(4-bromobutyl)-5,5-dimethyl-4-thiazolidinone (400 g), 1-(2-methylphenyl)-piperazine (3.87 g), K2CO3 (8.31 g), NaI (290 mg) and acetonitrile (175 ml) was heated at 75° C. (bath temperature) under nitrogen. After 16 hours, TLC analysis (silica gel, 5% MeOH/CH2Cl2) showed absence of the starting bromide and presence of a major product, Rf=0.24. The reaction mixture was cooled to room temperature, ethyl acetate (150 ml) was added, and the mixture filtered. The filtrate was concentrated in vacuo to in oil which was dissolved into ethyl acetate causing a solid to precipitate. The mixture was filtered and the filtrate concentrated in vacuo to 6.35 g of an oil. The oil was chromatographed (5% MeOH/CH2Cl2, one silica gel column) to obtain 4.91 g of a solid. The solid was dissolved in diethylether (550 ml), the solution filtered to remove a trace of insoluble material, and the filtrate acidified to pH=1 with a HCl/diethylether solution. The resulting salt was collected and dried to give 4.83 g of powder. The powder was recrystallized twice from ethanol/ethyl acetate to yield 2.14 g of crystals. m.p. 230-235° C.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe mixture filtered
  3. concentrationThe filtrate was concentrated in vacuo to in oil which
  4. dissolutionwas dissolved into ethyl acetate causing a solid
  5. customto precipitate
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate concentrated in vacuo to 6.35 g of an oil
  8. customThe oil was chromatographed (5% MeOH/CH2Cl2, one silica gel column)

Quellen und Nachweise

ORD-Eintrag
ord-15c81ef81a644d6ea37676d178397da0
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06284775B1

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