2-(Methylamino)ethanol → 2-[N-[Bis-(4-chlorophenyl)methyl]N-methylamino]ethanol

HRID 1383907Notes

Reaction equation

HRID 1383907 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6](Cl)[C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:17][NH:18][CH2:19][CH2:20][OH:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:18]([CH2:19][CH2:20][OH:21])[CH3:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 11430Potassium CarbonateHCID 130784,4'-Dichlorobenzhydryl chloride

Product 1

HCID 183189972-[N-[Bis-(4-chlorophenyl)methyl]N-methylamino]ethanolYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4,4′-dichlorobenzhydryl chloride (5.20 g, 19.1 mmol) and 2-(methylamino)ethanol (9.0 g, 0.106 mol) in acetonitrile (100 ml) was treated with powdered anhydrous potassium carbonate (10 g) and the resulting mixture was heated under reflux for 4 h. The cooled mixture was filtered and the filtrate was concentrated in vacuo. The residual oil was diluted with ethyl acetate, washed with water and brine and then dried over anhydrous magnesium sulfate. Evaporation of the solvent in vacuo followed by chromatography on silica gel (elution toluene-ethyl acetate 9:1) gave 4.29 g (79%) of the title material as a white solid: mp 49-50° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 4 h
  3. filtrationThe cooled mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionThe residual oil was diluted with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-ac697e4e425b454cb4cd33cece9939f7
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

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