Benzyl Bromide → N-Benzyl-N-(2,2,2-trifluoroethyl)-3-[4-(3,3-diphenyl-1-propyl)piperazin-1-yl]benzamide

HRID 1836810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1836810
[C:1]1([CH:7]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:17]=[C:18]([CH:27]=[CH:28][CH:29]=3)[C:19]([NH:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[O:20])[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH2:44](Br)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:44]([N:21]([CH2:22][C:23]([F:25])([F:26])[F:24])[C:19](=[O:20])[C:18]1[CH:27]=[CH:28][CH:29]=[C:16]([N:13]2[CH2:12][CH2:11][N:10]([CH2:9][CH2:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:15][CH2:14]2)[CH:17]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Komponenten

8

Edukt 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 221806393-[4-(3,3-diphenyl-1-propyl)piperazin-1-yl]-N-(2,2,2-trifluoroethyl)benzamide

Produkt 1

HCID 22180495N-Benzyl-N-(2,2,2-trifluoroethyl)-3-[4-(3,3-diphenyl-1-propyl)piperazin-1-yl]benzamideAusbeute 35,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

The compound (0.048 g) prepared in step (a) was dissolved in toluene (5 ml), and sodium hydroxide (0.014 g), potassium carbonate (0.028 g), tetrabutylammoniumhydrogen sulfate (0.003 g), and benzyl bromide (0.019 g) were added to the solution. The mixture was stirred at 60° C. for 3 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate, followed by washing with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then removed by distillation under the reduced pressure. The residue was purified by preparative TLC (hexane:ethyl acetate=1:2) to give 0.020 g (21.0%) of the title compound.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washby washing with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was then removed by distillation under the reduced pressure
  5. customThe residue was purified by preparative TLC (hexane:ethyl acetate=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-74874ca825b94c4bb678015347a54a5f
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06777414B1

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