2-(Dimethylamino)ethanol → HCID 68107476, compound

HRID 2403587Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][CH:3]=1.[NH:9]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.CN(C)CCO.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(=O)([O-])O.[Na+]>[Cu]>[I:8][C:5]1[CH:6]=[CH:7][C:2]([N:9]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Under an argon atmosphere, 1,4-diiodiobenzene (2 g), azepane (1.2 g), and 2-(dimethylamino)ethanol (5.3 g) were mixed, and tripotassium phosphate (2.8 g) and copper (77 mg) were added thereto, followed by stirring at 60° C. for 2 days. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with CHCl3. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain 1-(4-iodophenyl)azepane (300 mg).

Workup

extractionfollowed by extraction with CHCl3
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record: ord-8bcb6b0333974258acdc705e1839482f
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802679B2

Reaction notes

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