Toluene → p-Benzyl-ethylaminophenethyl alcohol

HRID 1174438Notes

Reaction equation

HRID 1174438 reaction equation
[NH2:1][C:2]1C=CC(CCO)=C[CH:3]=1.[C:11](=[O:14])([O-])[O-].[K+].[K+].C(I)C.[CH2:20](Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:28]1([CH3:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:20]([C:31]1[CH:32]=[CH:33][C:28]([CH2:34][CH:11]([OH:14])[NH:1][CH2:2][CH3:3])=[CH:29][CH:30]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 5

HCID 1140Toluene2×HCID 6340IodoethaneHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 669044-Aminophenethyl alcohol

Product 1

HCID 68771578p-Benzyl-ethylaminophenethyl alcohol

Conditions

Temperature
100 °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 50 mL of dehydrated toluene were poured, and the mixture was heated at 100° C. under an argon atmosphere with stirring. Then, 10.9 g (70 mmol) of ethyl iodide was delivered by drops into the reaction solution for 3 hours. Upon completion of the dripping, the reaction solution was further heated with stirring for 1 hour. Into the reaction solution, 10.9 g (70 mmol) of benzyl chloride was delivered by drops for 30 minutes. Upon completion of the dripping, the reaction solution was further heated with stirring for 3 hours. The reaction solution was cooled to the room temperature and then diluted with toluene, followed by washing with water five times. The toluene solution was dried with anhydrous magnesium sulfate, and then the solvent was distilled away to purify the toluene solution by silica gel chromatography using a mixture solvent of toluene/ethyl acetate (10/1) as an eluent to synthesize 6.69 g (yield: 37% by mass) of p-benzyl-ethylaminophenethyl alcohol.

Workup

  1. temperatureUpon completion of the dripping, the reaction solution was further heated
  2. stirringwith stirring for 1 hour
  3. temperatureUpon completion of the dripping, the reaction solution was further heated
  4. stirringwith stirring for 3 hours
  5. temperatureThe reaction solution was cooled to the room temperature
  6. washby washing with water five times
  7. dry with materialThe toluene solution was dried with anhydrous magnesium sulfate
  8. distillationthe solvent was distilled away
  9. customto purify the toluene solution by silica gel chromatography
  10. customto synthesize 6.69 g (yield: 37% by mass) of p-benzyl-ethylaminophenethyl alcohol

Sources & evidence

ORD record
ord-8d89c9257cfd4095b7426127b25025ed
Source dataset
uspto-grants-2010_11
Patent number
US07838188B2

Reaction notes

Loading…