Water → 4-[4-[4-(cis-2,6-Dimethylmorpholin-4-yl)phenyl]piperazin-1-yl]benzoic acid ethyl ester

HRID 1816752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1816752
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH2:3]1.[CH2:21]([O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][C:28](F)=[CH:27][CH:26]=1)[CH3:22].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.ClCCl>[CH2:21]([O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][C:28]([N:18]2[CH2:17][CH2:16][N:15]([C:12]3[CH:11]=[CH:10][C:9]([N:4]4[CH2:3][C@H:2]([CH3:1])[O:7][C@H:6]([CH3:8])[CH2:5]4)=[CH:14][CH:13]=3)[CH2:20][CH2:19]2)=[CH:27][CH:26]=1)[CH3:22]

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 67976Benzoic acid, 4-fluoro-, ethyl ester2×HCID 69677628cis-2,6-Dimethyl-4-(4-piperazinylphenyl)morpholine

Produkt 1

HCID 696777484-[4-[4-(cis-2,6-Dimethylmorpholin-4-yl)phenyl]piperazin-1-yl]benzoic acid ethyl esterAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of cis-2,6-dimethyl-4-(4-piperazinylphenyl)morpholine (2.00 g), 4-fluorobenzoic acid ethyl ester (1.43 g) and potassium carbonate (1.01 g) in dimethylsulfoxide (40 ml) was stirred for 8 hours at 150° C., during which period additional 4-fluorobenzoic acid ethyl ester (1.35 g) and potassium carbonate (1.0 g) was added to the mixture. The reaction mixture was added to a mixture of water and dichloromethane. The organic layer was taken and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (25:1 dichloromethane-methanol elution) to give 4-[4-[4-(cis-2,6-dimethylmorpholin-4-yl)phenyl]piperazin-1-yl]benzoic acid ethyl ester (2.5 g).

Aufarbeitung

  1. additionwas added to the mixture
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe magnesium sulfate was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (25:1 dichloromethane-methanol elution)

Quellen und Nachweise

ORD-Eintrag
ord-cdad8073772f4db6a2a501795a225214
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06884868B1

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