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

HRID 478111

Reaction equation

HRID 478111 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-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 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. [Dye (1)].

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-65cd0450302f40a4a7683d7e9e12f3f4
Source dataset
uspto-grants-2003_11
Patent number
US06641620B1

Linked notes

Loading…