Ethyl Bromide → N,N-Diethyl-m-phenetidine

HRID 621826

Reaction equation

HRID 621826 reaction equation
[CH2:1]([N:3]([CH2:11][CH3:12])[C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH3:20]>C(C(C)=O)C(C)C>[CH2:11]([N:3]([CH2:1][CH3:2])[C:4]1[CH:5]=[C:6]([O:10][CH2:19][CH3:20])[CH:7]=[CH:8][CH:9]=1)[CH3:12]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 70623-(Diethylamino)phenolHCID 11430Potassium Carbonate

Product 1

HCID 74625N,N-Diethyl-m-phenetidineYield 91.1%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A 1 liter reactor is charged with 300 ml of methyl isobutyl ketone, 73.1 g of 3-diethylaminophenol and 153.3 g of ground potassium carbonate and the mixture is stirred for 30 minutes. Then 72.7 g of ethyl bromide are introduced into the autoclave, which is then closed and heated for 3 hours to 115°-120° C. The temperature is then kept for a further 5 hours at 140°-142° C. (pressure: 5 bar). The contents of the autoclave are cooled to c. 25° C. and potassium bromide is removed by filtration. After washing with a small amount of methyl isobutyl ketone, the combined filtrates are concentrated by evaporation, to give 75.6 g (91.1% yield) of 3-diethylaminophenetol with a titre of 96.9%.

Workup

  1. customis then closed
  2. temperatureheated for 3 hours to 115°-120° C
  3. waitThe temperature is then kept for a further 5 hours at 140°-142° C.
  4. temperatureThe contents of the autoclave are cooled to c
  5. custom25° C. and potassium bromide is removed by filtration
  6. washAfter washing with a small amount of methyl isobutyl ketone
  7. concentrationthe combined filtrates are concentrated by evaporation

Sources & evidence

ORD record
ord-f5e0d1425a7d4291b9e97b8afe455367
Source dataset
uspto-grants-1989_04
Patent number
US04825005

Linked notes

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