1-Bromopropane → N-(2-ethylhexyl)-N-propylaniline

HRID 2258367

Reaction equation

HRID 2258367 reaction equation
[CH2:1]([CH:3]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:2].Br[CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([CH:3]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:4][N:5]([CH2:17][CH2:18][CH3:19])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 78401-Bromopropane2×HCID 11430Potassium CarbonateHCID 61484N-(2-Ethylhexyl)aniline

Product 1

HCID 53707404N-(2-ethylhexyl)-N-propylanilineYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of N-(2-ethylhexyl)aniline (8.9 parts), 1-bromopropane (7.4 parts), anhydrous potassium carbonate (11 parts) and N,N-dimethylformamide (30 parts) was stirred at 125° C. for 24 hours. An additional quantity of 1-bromopropane (5 parts) was added and the mixture stirred for a further 18 hours at 125° C. The cooled mixture was filtered and poured into water. The product was extracted into dichloromethane and evaporated to yield N-(2-ethylhexyl)-N-propylaniline (8.9 parts, 78%) which was reacted with acetic anhydride prior to use to remove any unreacted starting materials.

Workup

  1. stirringthe mixture stirred for a further 18 hours at 125° C
  2. filtrationThe cooled mixture was filtered
  3. additionpoured into water
  4. extractionThe product was extracted into dichloromethane
  5. customevaporated

Sources & evidence

ORD record
ord-d6483d1599d8480c890a96e246e7225f
Source dataset
uspto-grants-1997_08
Patent number
US05660598

Linked notes

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