Potassium Carbonate → Methyl 6-((2-ethylhexyl)(phenyl)amino)hexanoate

HRID 607493Notes

Reaction equation

[C:1]1([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH:25]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:26][CH3:27].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)(=O)C.O.CN(C)C=O>[CH2:26]([CH:25]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH3:27]

Participants

Conditions

Temperature: 100 °C

Procedure

In a three-neck flask, methyl 6-(phenylamino)hexanoate (25.0 g, 0.113 mmol) and potassium carbonate (25.0 g, 0.169 mol) were added to dimethylformamide (100 ml) and stirred. The mixture was heated to 100° C., added with 3-(bromomethyl)heptane (26.2 g, 0.135 mol), and allowed to react with stirring for 12 hours. The reaction product was transferred into a separate funnel, and was then added with water and ethyl acetate, after which the organic layer was isolated therefrom, dehydrated using sodium sulfate, and then distilled under reduced pressure. Subsequently, the obtained material was separated through silica column chromatography, thus obtaining 20.0 g of a yellowish transparent liquid.

Workup

customto react
stirringwith stirring for 12 hours
customThe reaction product was transferred into a separate funnel
customafter which the organic layer was isolated
distillationdistilled under reduced pressure
customSubsequently, the obtained material was separated through silica column chromatography

Sources & evidence

ORD record: ord-60022c30d19b4cdf9a31f0afe1b3f257
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915428B2

Reaction notes

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