Aniline → N-(2-Ethylhexyl)aniline

HRID 361272

Reaction equation

HRID 361272 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([CH:10]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:11]Br)[CH3:9].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:8]([CH:10]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:11][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:9]

Participants

5

Reactant 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 868042-Ethylhexyl bromide

Product 1

HCID 61484N-(2-Ethylhexyl)anilineYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of aniline (18.6 parts), 2-ethylhexyl bromide (42.4 parts), anhydrous potassium carbonate (30.3 parts) and dry N,N-dimethylformamide (100 parts) was stirred at 75° C. for 24 hours. The cooled mixture was filtered, diluted with dichloromethane and washed with 2N-hydrochloric acid (100 parts). The organic phase was evaported to leave oil which was triturated with petroleum ether and water to give N-(2-ethylhexyl)aniline (18 parts, 43%).

Workup

  1. filtrationThe cooled mixture was filtered
  2. additiondiluted with dichloromethane
  3. washwashed with 2N-hydrochloric acid (100 parts)
  4. customto leave oil which
  5. customwas triturated with petroleum ether and water

Sources & evidence

ORD record
ord-a1f10645be1845a384339f2e205461d5
Source dataset
uspto-grants-1999_02
Patent number
US05865857

Linked notes

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