Aniline → N,N-Dihexylaniline

HRID 1176168Notes

Reaction equation

HRID 1176168 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C([O-])([O-])=O.[K+].[K+]>CCO>[CH2:9]([N:1]([CH2:6][CH2:7][CH2:2][CH2:3][CH2:4][CH3:5])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 125271-Iodohexane

Product 1

HCID 138236N,N-Dihexylaniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of aniline (5.90 ml, 6.47×10−2 mol), 1-iodohexane (20.0 ml, 0.136 mol) and K2CO3 (18.80 g, 0.136 mol) in 80 ml of EtOH was refluxed for 27 h under Ar. The precipitate was filtered off and washed with CH2Cl2. The filtrate was washed with water and dried over Na2SO4. The residue was chromatographed on silica gel with 4:1 hexane:CHCl3 as the eluent. Yield=14.735 g (87% based on 5.90 ml of aniline). 1H NMR (250 MHz, CDCl3): δ 7.20 (dd, 2H, J=7.1, 8.8 Hz, Ph), 6.57-6.66 (m, 3H, Ph), 3.24 (t, 4H, J=7.7 Hz, —NCH2—), 1.48-1.65 (m, 4H, —NCH2CH2—), 1.22-1.40 (m, 12H, —CH2—), 0.90 (t, 6H, J=6.6 Hz, —CH3). CI MS m/z: 262.253 ((M+H)+) (calcd 262.253).

Workup

  1. temperaturewas refluxed for 27 h under Ar
  2. filtrationThe precipitate was filtered off
  3. washwashed with CH2Cl2
  4. washThe filtrate was washed with water
  5. dry with materialdried over Na2SO4
  6. customThe residue was chromatographed on silica gel with 4:1 hexane

Sources & evidence

ORD record
ord-2f47fc62a6684f50a97ba5863733e44e
Source dataset
uspto-grants-2010_11
Patent number
US07842758B2

Reaction notes

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