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

HRID 344241Notes

Reaction equation

HRID 344241 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[CH3:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:9][N:10]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 10340Sodium CarbonateHCID 748286-Chloro-1-hexanol

Product 1

HCID 152539786-[Methyl(phenyl)amino]hexan-1-OLYield 51.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Chlorohexyl alcohol (1.4 g), N-methylaniline (1.1 g) and sodium carbonate (1.1 g) were heated at 120° C. for 9 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 1.1 g of 6-(N-methy-N-phenylamino)hexyl alcohol.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5c9c6442828b40d5896f1f690c98f165
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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