Dimethylamine → 1,2-Ethanediamine,N2-(1,1-dimethylethyl)-N1,N1-dimethyl-

HRID 1446024Notes

Reaction equation

HRID 1446024 reaction equation
Cl.[C:2]([NH:6][CH2:7][CH2:8]Cl)([CH3:5])([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH3:16][NH:17][CH3:18]>>[C:2]([NH:6][CH2:7][CH2:8][N:17]([CH3:18])[CH3:16])([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 25021339HCID 25021339, compound

Product 1

HCID 206267161,2-Ethanediamine,N2-(1,1-dimethylethyl)-N1,N1-dimethyl-Yield 56%

Conditions

Temperature
140 °C

Procedure

2-(t-Butylamino)ethylchloride hydrochloride (1.2 g, 7.0 mmol) is dissolved in aqueous dimethylamine solution (40% by weight, 22 mL) in a sealed tube. The mixture is heated in a 140° C. oil bath for six hours, allowed to cool to room temperature, and then is saturated with solid potassium carbonate. The mixture is extracted thrice with ethyl acetate. The combined extracts are dried over anhydrous sodium sulfate, decanted, and concentrated under reduced pressure to give N-t-butyl,N′,N′-dimethylethylenediamine as a light brown liquid (0.57 g, 56%). The crude material is carried on to the following step without further purification.

Workup

  1. temperatureto cool to room temperature
  2. extractionThe mixture is extracted thrice with ethyl acetate
  3. dry with materialThe combined extracts are dried over anhydrous sodium sulfate
  4. customdecanted
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-40f60a6a7aa94965977c1c9486393b81
Source dataset
uspto-grants-2010_02
Patent number
US07666901B2

Reaction notes

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