Sodium Iodide → HCID 18348169, Verbindung

HRID 2267957

Reaktionsgleichung

Reaktionsgleichung von HRID 2267957
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8](Cl)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1.[N:17]1([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(N(CC)CC)C.[I-].[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl.CCCCCC>[CH2:26]([O:25][C:23]([N:17]1[CH2:18][CH2:19][N:20]([CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH2:21][CH2:22]1)=[O:24])[CH3:27]

Komponenten

8

Edukt 4

HCID 5238Sodium IodideHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 8471TriethylamineHCID 247330(2-Chlorophenyl)(4-chlorophenyl)methyl chloride

Produkt 1

HCID 18348169HCID 18348169, VerbindungAusbeute 28,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A stirred solution of 2.5 grams (0.009 mole) of (2-chlorophenyl)(4-chlorophenyl)methyl chloride, 1.6 grams (0.010 mole) of ethyl 1-piperazine-carboxylate, 1.4 mL (0.010 mole) of triethylamine, and 1.2 grams (0.008 mole) of sodium iodide in 25 mL of toluene was heated at reflux for about 18 hours. The resulting precipitate was collected by filtration. The filtrate was cooled to ambient temperature and 200 mL of aqueous saturated sodium bicarbonate solution was added to it. The mixture was extracted with two 100 mL portions of ethyl acetate. The combined ethyl acetate layers were washed with two 25 mL portions of an aqueous saturated sodium chloride solution. The organic layer was dried with sodium sulfate and concentrated under reduced pressure, yielding 3.2 grams of crude material. The crude material was subjected to column chromatography on silica gel with 50-25% hexane in methylene chloride, followed by pure methylene chloride, as eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding 1.0 gram of N-(ethoxycarbonyl)-N′-[(2-chlorophenyl)(4-chlorophenyl)methyl]piperazine. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. temperatureat reflux for about 18 hours
  2. filtrationThe resulting precipitate was collected by filtration
  3. addition200 mL of aqueous saturated sodium bicarbonate solution was added to it
  4. extractionThe mixture was extracted with two 100 mL portions of ethyl acetate
  5. washThe combined ethyl acetate layers were washed with two 25 mL portions of an aqueous saturated sodium chloride solution
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customyielding 3.2 grams of crude material
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-893a87e3b3c946a0b94bbe980dee7c6a
Quelldatensatz
uspto-grants-2001_12
Patentnummer
USH0002007H1

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