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

Participants

Role	Name	HCID	Charge
Reactant	4-Iodoaniline	HCID 10893	—
Reactant	1,2-Diaminocyclohexane, trans-	HCID 43806	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	1-Methyl-3-oxopiperazine	HCID 13704283	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	1-(4-Aminophenyl)-4-methyl-2-piperazinone	HCID 57590079	7%

Reaction Conditions

Temperature	110 °C

Reaction Steps

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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07612089B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-244f0c1f21e24a3b8c58103672302fbe
Source note	uspto-grants-2009_11