Amiodarone → HCID 14391628, Verbindung

HRID 232342

Reaktionsgleichung

Reaktionsgleichung von HRID 232342
[CH2:1]([C:5]1[O:6][C:7]2[CH:31]=[CH:30][CH:29]=[CH:28][C:8]=2[C:9]=1[C:10]([C:12]1[CH:17]=[C:16](I)[C:15]([O:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[C:14](I)[CH:13]=1)=[O:11])[CH2:2][CH2:3][CH3:4].[BH4-].[Na+]>CO.[Pd](Cl)Cl>[CH2:1]([C:5]1[O:6][C:7]2[CH:31]=[CH:30][CH:29]=[CH:28][C:8]=2[C:9]=1[CH:10]([C:12]1[CH:17]=[CH:16][C:15]([O:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:14][CH:13]=1)[OH:11])[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 2

HCID 2157AmiodaroneHCID 4311764Sodium borohydride

Produkt 1

HCID 14391628HCID 14391628, VerbindungAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24290Palladium ChlorideKatalysator2×HCID 887MethanolLösungsmittel

Versuchsvorschrift

One mmole (645 mg) of the ketone, (2-n-butyl-3-benzofuranyl) [4-[2-(diethylamino)ethoxyl]-3,5-diiodophenyl] methanone is dissolved in 10 ml of methanol. Palladium dichloride (2 mmole, 354 mg) is added and the mixture is agitated to suspend the palladium dichloride. The temperature of the mixture is adjusted to 20° C. Sodium borohydride (10 mmole, 379 mg) is added and stirring is continued until reaction is complete (~1 hour). The palladium dichloride is removed by filtration and water is added to the filtrate. An ether extraction is performed and the product is removed from the ether phase by evaporation under reduced pressure. The produce is purified by chromatography (silica gel using methylene chloride) and results in >50% yield of the product, m.p. 203° C. (decomposes).

Aufarbeitung

  1. customis adjusted to 20° C
  2. stirringstirring
  3. customis continued until reaction
  4. custom(~1 hour)
  5. customThe palladium dichloride is removed by filtration and water
  6. additionis added to the filtrate
  7. extractionAn ether extraction
  8. customthe product is removed from the ether phase by evaporation under reduced pressure
  9. customThe produce is purified by chromatography (silica gel using methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-4e3d02fbec6d4384a8a9b076b189621a
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04851554

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