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

HRID 361269

Reaction equation

HRID 361269 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-b013d208f9804c31a1bf4f08faa23737
Source dataset
uspto-grants-1999_02
Patent number
US05865857

Linked notes

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