Iodoethane → 4-(Diethylamino)phenethyl alcohol

HRID 1174436Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:18]1C=CC=C[CH:19]=1.[CH2:24](I)[CH3:25]>ClCCl>[CH2:18]([N:1]([CH2:24][CH3:25])[C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1)[CH3:19]

Participants

Conditions

Temperature: 120 °C

Procedure

In a four-aperture flask, 9.6 g (70 mmol) of p-aminophenethyl alcohol, 38.7 g (280 mmol) of potassium carbonate, and 100 mL of monochlorobenzene were poured, and the mixture was heated at 120° C. under an argon atmosphere with stirring. Then, 32.8 g (210 mmol) of ethyl iodide was delivered by drops into the mixture for 5 hours. Upon completion of the dripping, the mixture was further heated with stirring for 5 hours. The reaction solution was cooled to the room temperature and then diluted with dichloromethane, followed by washing with water three times. The dichloromethane solution was dried with anhydrous magnesium sulfate, the solvent was distilled away to purify the dichloromethane solution by silica gel chromatography using a mixture solvent of toluene/ethyl acetate (2/1) as an eluent to thereby synthesize 12.1 g (yield: 89% by mass) of p-diethylaminophenethyl alcohol.

Workup

temperatureUpon completion of the dripping, the mixture was further heated
stirringwith stirring for 5 hours
temperatureThe reaction solution was cooled to the room temperature
washby washing with water three times
dry with materialThe dichloromethane solution was dried with anhydrous magnesium sulfate
distillationthe solvent was distilled away
customto purify the dichloromethane solution by silica gel chromatography
customto thereby synthesize 12.1 g (yield: 89% by mass) of p-diethylaminophenethyl alcohol

Sources & evidence

ORD record: ord-07c07302c7794ba881d311d0210075a6
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07838188B2

Reaction notes

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