Diethyl Ether → ([1,1'-Biphenyl]-2-yl)-N,N,N-trimethylmethanaminium iodide

HRID 2418800Notes

Reaction equation

HRID 2418800 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][C:4]1[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:7]=[CH:8][CH:9]=1.C[I:18].[CH2:19](OCC)C>C(O)C>[I-:18].[CH3:1][N+:2]([CH3:19])([CH3:16])[CH2:3][C:4]1[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 9859729N,N-dimethyl-1-(2-phenylphenyl)methanamine

Product 1

HCID 13374112([1,1'-Biphenyl]-2-yl)-N,N,N-trimethylmethanaminium iodideYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a dry nitrogen atmosphere, 6.1 g (0.027 mole) of N,N-dimethyl-[1,1'-biphenyl]-2-methanamine was dissolved with stirring in 6.4 ml of anhydrous ethanol. To this solution 5.1 g (0.036 mole) of methyl iodide was added slowly. After complete addition, the reaction mixture was heated at reflux temperature for 45 minutes, then cooled. Diethyl ether was added until the mixture was cloudy, then the whole was placed in a freezer for 16 hours. An oil which had formed in the mixture was separated then dissolved in ethanol, and the solution was concentrated under reduced pressure to give 10.0 g (100% yield) of N,N,N-trimethyl-[1,1'-biphenyl]-2-methanaminium iodide as a brittle yellow foam.

Workup

  1. additionAfter complete addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux temperature for 45 minutes
  4. temperaturecooled
  5. customAn oil which had formed in the mixture
  6. customwas separated
  7. dissolutionthen dissolved in ethanol
  8. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0acac3871242481eba2ac290e776a2e4
Source dataset
uspto-grants-1984_09
Patent number
US04473709

Reaction notes

Loading…