Water → N,N-dimethyl-1-(2-phenylphenyl)methanamine

HRID 2418799Notes

Reaction equation

HRID 2418799 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]([C:5]1[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:8]=[CH:9][CH:10]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>COCCOC>[CH3:1][N:2]([CH3:17])[CH2:3][C:5]1[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 976212N,N-Dimethyl[1,1′-biphenyl]-2-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 9859729N,N-dimethyl-1-(2-phenylphenyl)methanamineYield 106.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Under a dry nitrogen atmosphere, 6.1 g (0.027 mole) of N,N-dimethyl-[1,1'-biphenyl]-2-carboxamide was dissolved with stirring in 250 ml of dry 1,2-dimethoxyethane. To this solution was added portionwise 1.3 g (0.034 mole) of lithium aluminum hydride. Upon complete addition, the reaction mixture was heated at reflux temperature for 18 hours. The reaction mixture was then cooled to room temperature, and 1.22 ml (0.068 mole) of water was added dropwise. The reaction mixture was filtered, and the filtrate concentrated under reduced pressure to give 6.1 g (100% yield) of N,N-dimethyl-[1,1'-biphenyl]-2-methanamine as a yellow liquid.

Workup

  1. additionUpon complete addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux temperature for 18 hours
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-d806958a46634229bb342e47827a58b5
Source dataset
uspto-grants-1984_09
Patent number
US04473709

Reaction notes

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