N-Methylaniline → 6-[Methyl(phenyl)amino]hexan-1-OL

HRID 1608458Notes

Reaction equation

HRID 1608458 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16].C(=O)([O-])[O-].[K+].[K+]>C(O)CCC.[I-].[K+]>[OH:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7515N-MethylanilineHCID 11430Potassium CarbonateHCID 748286-Chloro-1-hexanol

Product 1

HCID 152539786-[Methyl(phenyl)amino]hexan-1-OLYield 79.5%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 2631-ButanolSolvent

Procedure

N-(6-hydroxyhexyl)-N-methylaniline 2 was prepared by mixing N-methylaniline (153 g, 1.43 mol.), 6-chlorohexanol (200 g, 1.46 mol.), potassium carbonate (200 g, 1.45 mol.) and potassium iodide (6 g, catalyst) in 750 mL of n-butanol. The mixture was heated to reflux under argon with vigorous external stirring for 96 hours. The solution was cooled, filtered, and the solvent was removed in vacuo. The residue was distilled under high vacuum to yield 2 (235 g, 79.5% yield) as a colorless oil, having a boiling point of 120°-125° C. (0.05 mm Hg).

Workup

  1. customN-(6-hydroxyhexyl)-N-methylaniline 2 was prepared
  2. temperatureThe mixture was heated
  3. temperatureto reflux under argon with vigorous
  4. temperatureThe solution was cooled
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. distillationThe residue was distilled under high vacuum

Sources & evidence

ORD record
ord-27b126f7e1694ab3a09bf1456188e1b5
Source dataset
uspto-grants-1995_03
Patent number
US05395556

Reaction notes

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