N,N'-Dimethylethylenediamine → HCID 72950843, compound

HRID 56079Notes

Reaction equation

[CH2:1]([N:3]([CH2:6][C:7]1[CH:12]=[CH:11][C:10](I)=[CH:9][C:8]=1[F:14])[CH2:4][CH3:5])[CH3:2].[CH3:15][C:16]1[C:17](=[O:23])[NH:18][CH:19]=[C:20]([CH3:22])[CH:21]=1.CNCCNC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I.C(Cl)Cl>[CH2:1]([N:3]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:18]2[CH:19]=[C:20]([CH3:22])[CH:21]=[C:16]([CH3:15])[C:17]2=[O:23])=[CH:9][C:8]=1[F:14])[CH2:4][CH3:5])[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of N-ethyl-N-(2-fluoro-4-iodobenzyl)ethanamine (1.72 g, 5.60 mmol) in dioxane (50 mL) was added 3,5-dimethyl-pyridone (0.69 g, 5.60 mmol), N,N′-dimethyl ethane-1,2-diamine (0.20 g, 2.24 mmol), CuI (0.21 g, 1.12 mmol) and potassium phosphate (2.38 g, 11.20 mmol) under N2. The reaction mixture was heated at 110° C. for 9 h, then cooled to rt and poured into CH2Cl2 (200 mL). The mixture was filtered, and the filtrate was washed with water (200 mL×3) and brine (200 mL). The organic phase was concentrated in vacuo. The residue was purified by a silica gel column chromatography (CH2Cl2/MeOH (V/V)=10:1) to give the title compound as a yellow solid (0.23 g, 14%). The compound was characterized by the following spectroscopic data:

Workup

temperaturecooled to rt
filtrationThe mixture was filtered
washthe filtrate was washed with water (200 mL×3) and brine (200 mL)
concentrationThe organic phase was concentrated in vacuo
customThe residue was purified by a silica gel column chromatography (CH2Cl2/MeOH (V/V)=10:1)

Sources & evidence

ORD record: ord-d8c55eb0ee28480caf5c4cd07449b078
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

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