Sodium Hydroxide → 1-[2-(dimethylamino)ethoxy]-N,N,2-trimethylpropane-2-amine

HRID 541106

Reaction equation

HRID 541106 reaction equation
[OH-].[Na+].[CH3:3][N:4]([CH3:10])[C:5]([CH3:9])([CH3:8])[CH2:6][OH:7].Cl.[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15]Cl>C1(C)C=CC=CC=1>[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][O:7][CH2:6][C:5]([CH3:9])([N:4]([CH3:10])[CH3:3])[CH3:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 234352-(Dimethylamino)-2-methylpropanolHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 866576141-[2-(dimethylamino)ethoxy]-N,N,2-trimethylpropane-2-amineYield 27%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To toluene (100 ml), sodium hydroxide (16.7 g, 418 mmol) and 2-dimethylamino-2-methyl-1-propanol (23.4 g, 200 mmol) were added and the mixture was heated at reflux for 2 hours. After cooling to 70° C., β-dimethylaminoethyl chloride hydrochloride (28.8 g, 200 mmol) was added. Then, the mixture was heated at reflux for 5.5 hours. After cooling to room temperature, insolubles were separated by filtration and the organic phase was concentrated under reduced pressure. The residue was distilled under reduced pressure to obtain 10.3 g (in a yield of 27%) of the objective compound as a colorless liquid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperatureThen, the mixture was heated
  4. temperatureat reflux for 5.5 hours
  5. temperatureAfter cooling to room temperature
  6. custominsolubles were separated by filtration
  7. concentrationthe organic phase was concentrated under reduced pressure
  8. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-dc8c5e0dd9064b429536880dde457406
Source dataset
uspto-grants-2014_10
Patent number
US08871970B2

Linked notes

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