Iodoethane → HCID 69012300, compound

HRID 2096102Notes

Reaction equation

HRID 2096102 reaction equation
[NH2:1][C:2]1([O:9][CH2:10][CH3:11])[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:19]1C=CC=C[CH:20]=1.[CH2:25](I)[CH3:26]>ClCCl>[CH2:19]([N:1]([CH2:25][CH3:26])[C:2]1([O:9][CH2:10][CH3:11])[CH:3]=[CH:4][C:5]([OH:8])=[CH:6][CH2:7]1)[CH3:20]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 7964ChlorobenzeneHCID 11430Potassium CarbonateHCID 66789000HCID 66789000, compound

Product 1

HCID 69012300HCID 69012300, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A four-necked flask was charged with 9.6 g (70 mmol) of p-aminophenetyl alcohol, 38.7 g (280 mmol) of potassium carbonate and 100 ml of monochlorobenzene under argon gas atmosphere, and heated at 120° C. with agitation. To the flask was added dropwise 32.8 g (210 mmol) of ethyl iodide over 5 hours, and after addition, heated for 5 hours with agitation. The reaction solution was cooled to room temperature, diluted with dichloromethane, and washed with water three times. The dichloromethane solution was dried with anhydrous magnesium sulfate followed by solvent removal, and purified by column chromatography on silica gel using mixture solvent of toluene/ethyl acetate (2/1) to give 12.1 g of p-diethylaminophenetyl alcohol (yield=89% by mass).

Workup

  1. additionafter addition
  2. temperatureheated for 5 hours with agitation
  3. temperatureThe reaction solution was cooled to room temperature
  4. washwashed with water three times
  5. dry with materialThe dichloromethane solution was dried with anhydrous magnesium sulfate
  6. customfollowed by solvent removal
  7. custompurified by column chromatography on silica gel using mixture solvent of toluene/ethyl acetate (2/1)

Sources & evidence

ORD record
ord-12b73846424d4f3a857e14bd8613eb5d
Source dataset
uspto-grants-2013_05
Patent number
US08450033B2

Reaction notes

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