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

HRID 621827

Reaction equation

HRID 621827 reaction equation
[CH2:1](C(C)=O)[CH:2](C)C.[CH2:8]([N:10]([CH2:18][CH3:19])[C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1)[CH3:9].C(=O)([O-])[O-].[K+].[K+].C(Br)C>O>[CH2:18]([N:10]([CH2:8][CH3:9])[C:11]1[CH:12]=[C:13]([O:17][CH2:1][CH3:2])[CH:14]=[CH:15][CH:16]=1)[CH3:19]

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 70623-(Diethylamino)phenolHCID 7909Methyl Isobutyl KetoneHCID 11430Potassium Carbonate

Product 1

HCID 74625N,N-Diethyl-m-phenetidineYield 97.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1 liter reactor is charged with 150 ml of methyl isobutyl ketone, 73.1 g of 3-diethylaminophenol and 153.3 g of ground potassium carbonate. The mixture is stirred for 30 minutes, then 72.7 g of ethyl bromide are added and the autoclave is closed. The reaction mixture is heated first for 3 hours to 115°-129° C. and then for a further 5 hours at 140°-142° C. (pressure: 4 bar). After cooling to c. 25° C. and addition of water, the product is isolated with the organic phase, which is washed with water and concentrated by evaporation, to give 80.67 g (97.2% yield) of 3-diethylaminophenetol with a titre of 94.8%.

Workup

  1. customthe autoclave is closed
  2. temperatureThe reaction mixture is heated first for 3 hours to 115°-129° C.
  3. waitfor a further 5 hours at 140°-142° C. (pressure: 4 bar)
  4. temperatureAfter cooling to c
  5. customthe product is isolated with the organic phase, which
  6. washis washed with water
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-9b67ac91caa046579f6521cfa6e7bc7f
Source dataset
uspto-grants-1989_04
Patent number
US04825005

Linked notes

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