Potassium Carbonate → HCID 178456386, Verbindung

HRID 1984037Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984037
I[C:2]1[CH:25]=[CH:24][C:5]([O:6][CH:7]2[CH2:12][CH2:11][CH:10]([C:13]([N:15]3[CH2:20][CH2:19][N:18]([CH:21]([CH3:23])[CH3:22])[CH2:17][CH2:16]3)=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C:27]1=[O:32].C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O.[Cu]>[CH:21]([N:18]1[CH2:19][CH2:20][N:15]([C:13]([C@H:10]2[CH2:11][CH2:12][C@H:7]([O:6][C:5]3[CH:24]=[CH:25][C:2]([N:26]4[CH2:31][CH2:30][CH2:29][CH2:28][C:27]4=[O:32])=[CH:3][CH:4]=3)[CH2:8][CH2:9]2)=[O:14])[CH2:16][CH2:17]1)([CH3:23])[CH3:22]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 126652-PiperidoneHCID 68443233HCID 68443233, Verbindung

Produkt 1

HCID 178456386HCID 178456386, VerbindungAusbeute 46,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 1.04 g (4.09 mmol) of cis-(4-isopropyl-piperazin-1-yl)-(4-hydroxy-cyclohexyl)-methanone, 1.50 g (6.82 mmol) of 4-iodephenol, 1.25 g (4.77 mmol) of triphenylphisphine in 5 ml THF, 1.1 g (4.78 mmol) of di-tert-butyl azodicarboxylate was added at 0° C., and stirred for 12 h at room temperature. After evaporation, the residue was purified by column chromatography on silica gel eluting with cyclohexane and ethyl acetate=from 100:0 to 2:1. The combined product fractions were evaporated to dryness to yield 0.67 g (14% yields, about 67% purity) of [4-(4-iodo-phenoxy)-cyclohexyl]-(4-isopropyl-piperazin-1-yl)-methanone. A mixture 100 mg (0.15 mmol) of [4-(4-iodo-phenoxy)-cyclohexyl]-(4-isopropyl-piperazin-1-yl)-methanone, 87 mg (0.88 mmol) of 2-piperidone, 41 mg (0.3 mmol) of potassium carbonate and 37 mg (0.58 mmol) of copper was stirred at 175 degree for 6 hr. The mixture was diluted with AcOEt, filtered through celite. The filtrate was washed with saturated NaHCO3 solution and brine, dried over MgSO4, and evaporated. The residue was purified by column chromatography on silica eluting with cyclohexane and ethyl acetate=from 100:0 to 1:3. The combined product fractions were evaporated to dryness to yield 30 mg (32%) of the title compound. MS (m/e): 428.3 (MH+).

Aufarbeitung

  1. filtrationfiltered through celite
  2. washThe filtrate was washed with saturated NaHCO3 solution and brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica eluting with cyclohexane and ethyl acetate=from 100:0 to 1:3
  6. customThe combined product fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-39587347bd9040eea83ce3a057a0c3b5
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544683B2

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