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

HRID 361268

Reaction equation

HRID 361268 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 potassium carbonate (65 parts) and DMF (150 parts) was stirred while heating under reflux for 41 hours. An additional quantity of 1-bromobutane (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 parts) 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 parts)
  10. custombefore evaporating

Sources & evidence

ORD record
ord-b7b5a11f9d18498f85d5702124a3af82
Source dataset
uspto-grants-1999_02
Patent number
US05865857

Linked notes

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