Ethylene Glycol → 3-[2-(4-bromophenyl)-1,3-dioxolan-2-yl]-N,N-diethylpropan-1-amine

HRID 70572Notes

Reaction equation

[CH2:1]([OH:4])[CH2:2][OH:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=O)[CH2:25][CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:20][CH:19]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Br:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2([CH2:25][CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[O:4][CH2:1][CH2:2][O:3]2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Ethylene glycol (10 mL) and p-toluenesulfonic acid monohydrate (128 mg) were added to a solution of 1-(4-bromophenyl)-4-(diethylamino)butan-1-one (2.0 g) in toluene (80 mL), and the mixture was stirred at 150° C. for one hour. The reaction solution was cooled to room temperature and p-toluenesulfonic acid monohydrate (1.28 g) was added, after which the mixture was stirred at 150° C. for further one hour. The reaction solution was cooled to room temperature and neutralized with saturated aqueous sodium bicarbonate, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to give the title compound as a brown oil (2.09 g, 91%).

Workup

temperatureThe reaction solution was cooled to room temperature
stirringafter which the mixture was stirred at 150° C. for further one hour
extractionfollowed by extraction with chloroform
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
customThe solvent was then evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record: ord-d04b8a6eb8924dedad28ee4afc3226fb
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Reaction notes

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