N,N'-Dimethylethylenediamine → N~1~-(Diphenylmethyl)-N~1~,N~2~-dimethylethane-1,2-diamine

HRID 2251951Notes

Reaction equation

HRID 2251951 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][NH:5][CH3:6].C(=O)([O-])[O-].[K+].[K+].[CH:13](Br)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH:13]([N:2]([CH3:1])[CH2:3][CH2:4][NH:5][CH3:6])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 236603Bromodiphenylmethane

Product 1

HCID 13984386N~1~-(Diphenylmethyl)-N~1~,N~2~-dimethylethane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15.1 g (171 mmol) N,N′-dimethylethylenediamine, 35 g (255 mmol) potassium carbonate are placed in 250 ml DMF and 30.9 g (125 mmol) benzhydryl bromide are added dropwise at RT. The mixture is concentrated under vacuum. The residue is taken up in chloroform and washed with water. The organic phase is dried over sodium sulfate and the solvent is removed under vacuum. The purification occurs by chromatography on silica gel with chloroform: Yield 14.5 g (45%).

Workup

  1. concentrationThe mixture is concentrated under vacuum
  2. washwashed with water
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customthe solvent is removed under vacuum
  5. customThe purification

Sources & evidence

ORD record
ord-85ba89e49b8c49ecb4ccd358a01b2230
Source dataset
uspto-grants-2008_01
Patent number
US07320993B1

Reaction notes

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