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

HRID 414433Notes

Reaction equation

HRID 414433 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) of 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-0b90ee46b8a94ff18a2eae6cb02a2554
Source dataset
uspto-grants-1988_12
Patent number
US04792208

Reaction notes

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