Diethylamine → 2,2-Diethoxyethyl(diethyl)amine

HRID 1722843Notes

Reaction equation

HRID 1722843 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-88757d42c39d4d358c8507f753ba02b4
Source dataset
uspto-grants-1989_08
Patent number
US04857663

Reaction notes

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