Diethylamine → 2,2-Diethoxyethyl(diethyl)amine

HRID 484754Notes

Reaction equation

HRID 484754 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5]Br)[CH3:2].[CH2:10]([NH:12][CH2:13][CH3:14])[CH3:11]>>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][N:12]([CH2:13][CH3:14])[CH2:10][CH3:11])[CH3:2]

Participants

3

Reactant 2

HCID 8021DiethylamineHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 771642,2-Diethoxyethyl(diethyl)amineYield 72.8%

Conditions

Temperature
40 °C

Procedure

Bromoacetaldehyde diethylacetal, 52.4 g (0.26 mol), was mixed carefully with approximately 70.7 g (0.967 mol) diethylamine and stirred at 40° C. overnight. The reaction mixture was concentrated under reduced pressure and the residue dissolved in water and basified with cold 5N sodium hydroxide. The reaction mixture was extracted twice with diethyl ether, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a tan oil. Distillation gave 35.8 g (72.8%) diethylaminoacetaldehyde diethylacetal as a clear liquid. B.p. 65°-75° C. @ 1.0 mmHg.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue dissolved in water and basified with cold 5N sodium hydroxide
  3. extractionThe reaction mixture was extracted twice with diethyl ether
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a tan oil
  7. distillationDistillation

Sources & evidence

ORD record
ord-b8362daa2ff14d6793a2fdc37ea197da
Source dataset
uspto-grants-1985_08
Patent number
US04533677

Reaction notes

Loading…