Dimethylformamide → N-Butyl-N-(heptan-2-YL)aniline

HRID 1356928

Reaction equation

HRID 1356928 reaction equation
[CH3:1][CH:2]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Br[CH2:16][CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:16]([N:8]([CH:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8002Butyl bromide2×HCID 11430Potassium CarbonateHCID 11344519N-(2-Heptyl)aniline

Product 1

HCID 18000381N-Butyl-N-(heptan-2-YL)anilineYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-(1-methylhexyl)aniline (76 parts) 1-bromobutane (66 parts), anhydrous potasium carbonate (65 parts) and DMF (150 parts) was stirred while heating under reflux for 41 hours. An additional quantity of 1-bromo butane (44 parts) was added and the mixture stirred while heating under reflux for a further 19 hours. The cooled mixture was poured into water (400 parts) and the organic phase separated. The aqueous phase was extracted with toluene, the organic phases and toluene extract were combined and washed with water (2×100 arts) before evaporating to leave N-butyl-N-(1-methylhexyl)aniline (72.8 parts, 44%) which was purified by vacuum distillation to give N-butyl-N-(1-methylhexyl)aniline b.pt 73-80° C., 2.6 mm Hg.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux for 41 hours
  3. stirringthe mixture stirred
  4. temperaturewhile heating
  5. temperatureunder reflux for a further 19 hours
  6. customthe organic phase separated
  7. extractionThe aqueous phase was extracted with toluene
  8. extractionthe organic phases and toluene extract
  9. washwashed with water (2×100 arts)
  10. custombefore evaporating

Sources & evidence

ORD record
ord-3ff9c2ee28d742bc8f195bc18c3d982e
Source dataset
uspto-grants-2003_07
Patent number
US06589296B1

Linked notes

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