Toluene → 1-[N-(2-trifluoromethylphenyl)-N-cyclohexylcarbonyl-2-aminoethyl]-4-(2-methoxyphenyl)piperazine

HRID 1420576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1420576
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11].Cl[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][N:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35][CH3:36])[CH2:25][CH2:24]1.[OH-].[Na+].C1(C)C=CC=CC=1>CC[N+](CC1C=CC=CC=1)(CC)CC.[Cl-].O>[F:1][C:2]([F:18])([F:19])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]([C:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:21][CH2:22][N:23]1[CH2:24][CH2:25][N:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35][CH3:36])[CH2:27][CH2:28]1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 5956731-(2-Chloroethyl)-4-(2-methoxyphenyl)piperazineHCID 1367212N-[2-(trifluoromethyl)phenyl]cyclohexanecarboxamide2×

Produkt 1

HCID 224581051-[N-(2-trifluoromethylphenyl)-N-cyclohexylcarbonyl-2-aminoethyl]-4-(2-methoxyphenyl)piperazineAusbeute 33,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of N-(2-trifluoromethylphenyl)cyclohexanecarboxamide (0.2 g) (compd 26A), 1-(2-chloroethyl)-4-(2-methoxyphenyl)piperazine (0.37 g), 50% (w/w) NaOH (0.5 mL), TEBAC (0.16 g) and toluene (2 mL) was stirred at 80° C. for 3.5 h. An additional amount of compd 26A (0.2 g) was then added and after 6 h stirring at 80° C. The mixture was poured into H2O and extracted with CH2Cl2. The organic phase was dried on anhydrous Na2SO4, evaporated to dryness and the residue purified by flash chromatography (EtOAc-petroleum ether 3:7) giving 0.12 g (17%) of the title compound.

Aufarbeitung

  1. stirringstirring at 80° C
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic phase was dried on anhydrous Na2SO4
  4. customevaporated to dryness
  5. customthe residue purified by flash chromatography (EtOAc-petroleum ether 3:7)

Quellen und Nachweise

ORD-Eintrag
ord-5908c911585d407183a131013bc9feb6
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06071920

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