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

HRID 1199284Notes

Reaction equation

HRID 1199284 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+]>[I-].[K+].C(O)CCC>[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 71%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 2631-ButanolSolvent

Procedure

A mixture of 153 g (1.43 mol) freshly distilled N-methylaniline, 200 g (1.46 mol) 6-chlorohexanol, 200 g (1.45 mol) potassium carbonate, 6 g potassium iodide, and 750 mL n-butanol was heated at reflux under nitrogen with vigorous mechanical stirring for 4 days. The solution was cooled, filtered, and the solvent was removed at reduced pressure. The residue was distilled in vacuo to produce 210 g (71%) of a colorless oil, bp 153°-166° C. (0.10 mm).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen with vigorous
  3. temperatureThe solution was cooled
  4. filtrationfiltered
  5. customthe solvent was removed at reduced pressure
  6. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-72bc5160414e497780c15ea95cbbeb2d
Source dataset
uspto-grants-1990_02
Patent number
US04900127

Reaction notes

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