Aniline → N,N-dihexadecylaniline

HRID 329353Notes

Reaction equation

HRID 329353 reaction equation
N[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][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C([N:28]([CH:31]([CH3:33])[CH3:32])[CH2:29][CH3:30])(C)C>C1(C)C=CC=CC=1>[CH2:9]([N:28]([CH2:29][CH2:30][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:2])[C:31]1[CH:32]=[CH:11][CH:10]=[CH:9][CH:33]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 6115AnilineHCID 110071-IodohexadecaneHCID 81531Diisopropylethylamine

Product 1

HCID 5102033N,N-dihexadecylanilineYield 48%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Aniline (0.93 g), 1-iodohexadecane (10.56 g) and diisopropylethylamine (2.58 g) were combined in 10 ml of toluene. The mixture was heated at about 100° C. for a period of three days. The mixture was chromatographed on a silica gel column using 1% ethyl acetate in hexane. The heavy crystalline mass that precipitated from solution was cooled, diluted with ether and filtered. The filtrate was concentrated to an oil and applied to a silica gel column. The oil was washed with 500 ml of hexane followed by 1% ethyl acetate in hexane. The dialkylated fractions were combined and evaporated to give 2.6 grams of product.

Workup

  1. customThe mixture was chromatographed on a silica gel column
  2. customThe heavy crystalline mass that precipitated from solution
  3. temperaturewas cooled
  4. additiondiluted with ether
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated to an oil
  7. washThe oil was washed with 500 ml of hexane
  8. customevaporated

Sources & evidence

ORD record
ord-e85b1ee711064a0684646b2befec4d4a
Source dataset
uspto-grants-1990_01
Patent number
US04891324

Reaction notes

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