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

HRID 478112

Reaction equation

HRID 478112 reaction equation
[CH2:1]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Br[CH:19]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH3:20].CN(C=O)C>O>[CH2:1]([N:5]([CH:19]([CH3:20])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 14310N-ButylanilineHCID 160902-Bromoheptane

Product 1

HCID 18000381N-Butyl-N-(heptan-2-YL)anilineYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of N-butylaniline (7.45 parts) anhydrous potassium carbonate (7.5 parts), 2-bromoheptane (13.5 parts) and DMF (25 parts) was stirred at 130° C. for 86 hours. The reaction mixture was poured into water, saturated with salt and extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4) and evaporated to leave N-butyl-N-(1-methylhexyl)aniline (11.8 parts, approximately 60% strength). This material had acetic anhydride (10 parts) added to it prior to further use.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-b5b9ca4822df44e1bacd2841c36c81b6
Source dataset
uspto-grants-2003_11
Patent number
US06641620B1

Linked notes

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