Water → Ethyl 2-((3-(benzyloxy)phenyl)(ethyl)amino)acetate

HRID 709642Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:29][CH3:30].O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([N:15]([CH2:29][CH3:30])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of ethyl 2-((3-(benzyloxy)phenyl)amino)acetate (1.00 g) in DMF (10 mL) were added potassium carbonate (970 mg) and iodoethane (2.20 g), and the mixture was stirred at 120° C. for 4 hr. The mixture was allowed to cool to room temperature, and water was added. The reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (960 mg) as a colorless oil.

Workup

temperatureto cool to room temperature
extractionThe reaction mixture was extracted with ethyl acetate
washthe extract was washed with saturated brine
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-5bf406838ac742998d0f818b6b60bbc8
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181186B2

Reaction notes

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