Diethylamine → 2,2-Diethoxyethyl(diethyl)amine

HRID 2232669Notes

Reaction equation

HRID 2232669 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 5 N 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 5 N 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-88f029f0c1fc4de69ced9fe1a375e41f
Source dataset
uspto-grants-1988_11
Patent number
US04788335

Reaction notes

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