Potassium Iodide → 6-[Methyl(phenyl)amino]hexan-1-OL

HRID 1109853Notes

Reaction equation

HRID 1109853 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 4

HCID 4875Potassium IodideHCID 7515N-MethylanilineHCID 11430Potassium CarbonateHCID 748286-Chloro-1-hexanol

Product 1

HCID 152539786-[Methyl(phenyl)amino]hexan-1-OL

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 153 g (1.43 mol) freshly distilled N-methylaniline, 200 g (1.46) 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 a colorless oil.

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
  7. customto produce a colorless oil

Sources & evidence

ORD record
ord-dbdbf336a23f46e483b1676b6ce2698e
Source dataset
uspto-grants-1994_06
Patent number
US05322986

Reaction notes

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