Sodium Iodide → (4-Iodo-2-methylphenyl)-[2-(4-methylpiperidin-1-yl)ethyl]amine

HRID 734825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734825
[Na+].[I-:2].CNCCNC.Br[C:10]1[CH:15]=[CH:14][C:13]([NH:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([CH3:25])[CH2:21][CH2:20]2)=[C:12]([CH3:26])[CH:11]=1>O1CCOCC1.CCOC(C)=O.[Cu]I>[I:2][C:10]1[CH:15]=[CH:14][C:13]([NH:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([CH3:25])[CH2:21][CH2:20]2)=[C:12]([CH3:26])[CH:11]=1

Komponenten

7

Edukt 3

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 69054033(4-Bromo-2-methylphenyl)-[2-(4-methylpiperidin-1-yl)ethyl]amine

Produkt 1

HCID 69059102(4-Iodo-2-methylphenyl)-[2-(4-methylpiperidin-1-yl)ethyl]amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

73 mg (0.386 mmol) of CuI, 1.16 g (7.71 mmol) of NaI, and N,N′-dimethylethane-1,2-diamine were added under argon to a solution of 1.20 g (3.86 mmol) of (4-bromo-2-methylphenyl)-[2-(4-methylpiperidin-1-yl)ethyl]amine in 3.9 mL of 1,4-dioxane and the mixture was stirred for 20 hours at 110° C. The reaction mixture was cooled to RT and diluted with EtOAc. The organic phase was washed with 10% aqueous ammonia, dried over magnesium sulfate, and evaporated down in vacuo. Yield: 1.22 g (88% of theoretical); C15H23IN2 (M=358.261); calc.: molpeak (M+H)+: 359; found: molpeak (M+H)+: 359; HPLC-MS: 6.24 minutes (method A).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to RT
  2. washThe organic phase was washed with 10% aqueous ammonia
  3. dry with materialdried over magnesium sulfate
  4. customevaporated down in vacuo
  5. custom6.24 minutes (method A)

Quellen und Nachweise

ORD-Eintrag
ord-80f30f2375254e768b98961b4ae5f607
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592358B2

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