Sodium Iodide → 6-Iodo-4-methyl-2-(4-methylpiperidin-1-yl)quinoline

HRID 2112820Notes

Reaction equation

[Na+].[I-:2].CNCCNC.Br[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([N:20]1[CH2:25][CH2:24][CH:23]([CH3:26])[CH2:22][CH2:21]1)[CH:14]=[C:13]2[CH3:27].CCOC(C)=O>O1CCOCC1.[Cu]I>[I:2][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([N:20]1[CH2:25][CH2:24][CH:23]([CH3:26])[CH2:22][CH2:21]1)[CH:14]=[C:13]2[CH3:27]

Participants

Conditions

Temperature: 110 °C

Procedure

Under an argon atmosphere, 39 mg (0.2 mmol) of CuI, 0.6 g (4.0 mmol) of NaI, and 43 μL N,N′-dimethylethylenediamine are added to a solution of 0.69 g (2.0 mmol) of 6-bromo-4-methyl-2-(4-methylpiperidin-1-yl)quinoline in 2 mL of 1,4-dioxane and the reaction mixture is shaken for 14 hours at 110° C. After cooling, it is combined with 60 mL of EtOAc, and the organic phase is washed twice with 20 mL of 5% NH3 solution and dried over magnesium sulfate. After the desiccant and solvent have been eliminated, the residue is reacted further without purification. Yield: 0.65 g (88% of theoretical); C16H19IN2 (M=366.240); calc.: molpeak (M+H)+: 367; found: molpeak (M+H)+: 367; HPLC-MS: 7.0 min (method A).

Workup

temperatureAfter cooling
washthe organic phase is washed twice with 20 mL of 5% NH3 solution
dry with materialdried over magnesium sulfate
customthe residue is reacted further without purification
custom7.0 min (method A)

Sources & evidence

ORD record: ord-413cbaef4ca045f0a9f6fb3e183d45ef
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524862B2

Reaction notes

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