4-Iodoaniline → HCID 69056303, compound

HRID 1432560Notes

Reaction equation

HRID 1432560 reaction equation
I[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH3:9][N:10]1[CH2:16][CH2:15][CH2:14][NH:13][C:12](=[O:17])[CH2:11]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].N[C@@H]1CCCC[C@H]1N>O1CCOCC1.[Cu]I>[CH3:9][N:10]1[CH2:16][CH2:15][CH2:14][N:13]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=2)[C:12](=[O:17])[CH2:11]1

Participants

7

Reactant 4

HCID 108934-IodoanilineHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 122365174-methyl-2-homopiperazinone

Product 1

HCID 69056303HCID 69056303, compoundYield 15.2%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 4-iodoaniline (70 mg, 0.32 mmol), 4-methyl-2-homopiperazinone (35 mg, 0.27 mmol), K3PO4 (135 mg, 0.64 mmol) and 1,2-trans-diaminocyclohexane (16 uL, 0.13 mmol) in dioxane (4 mL) was degassed with Ar before being charged with CuI (18 mg, 0.095 mmol). The mixture in a sealed tube was heated at 110 C overnight. The mixture was then purified by a silica gel prep-TLC using CH2Cl2/MeOH (95/5) as solvents to give the titled compound (9 mg). MS 220.5 (M+H).

Workup

  1. customwas degassed with Ar
  2. temperatureThe mixture in a sealed tube was heated at 110 C overnight
  3. customThe mixture was then purified by a silica gel prep-TLC

Sources & evidence

ORD record
ord-e3712b00c5f04b2895325644a27b2321
Source dataset
uspto-grants-2009_11
Patent number
US07612089B2

Reaction notes

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