4-Iodoaniline → 1-(4-Aminophenyl)-4-methyl-2-piperazinone

HRID 1432559Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432559
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][C:4](=[O:8])[CH2:3]1.I[C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].N[C@@H]1CCCC[C@H]1N>O1CCOCC1.[Cu]I>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:10]2[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=2)[C:4](=[O:8])[CH2:3]1

Komponenten

7

Edukt 4

HCID 108934-IodoanilineHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 137042831-Methyl-3-oxopiperazine

Produkt 1

HCID 575900791-(4-Aminophenyl)-4-methyl-2-piperazinoneAusbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 4-methyl-2-piperazinone (200 mg, 1.75 mmol), 4-iodoaniline (384 mg, 1.75 mmol), K3PO4 (848 mg, 4.00 mmol) and 1,2-trans-diaminocyclohexane (98 uL, 0.80 mmol) in dioxane (6 mL) was degassed with Ar before being charged with CuI (76 mg, 0.40 mmol). The mixture in a sealed tube was heated at 110° C. for 4 h. It was then purified by a silica gel prep-TLC using CH2Cl2/MeOH (95/5) as solvents to give the desired product (25 mg). MS 206.2 (M+H).

Aufarbeitung

  1. customwas degassed with Ar
  2. customIt was then purified by a silica gel prep-TLC

Quellen und Nachweise

ORD-Eintrag
ord-244f0c1f21e24a3b8c58103672302fbe
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612089B2

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