Diethylamine → 3-Diethylamino-N,N-Dimethylpropionamide

HRID 1075774Notes

Reaction equation

HRID 1075774 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[CH3:6][N:7]([CH3:12])[C:8](=[O:11])[CH:9]=[CH2:10]>>[CH2:1]([N:3]([CH2:4][CH3:5])[CH2:10][CH2:9][C:8]([N:7]([CH3:12])[CH3:6])=[O:11])[CH3:2]

Participants

3

Reactant 2

HCID 8021DiethylamineHCID 17587N,N-Dimethylacrylamide

Product 1

HCID 214492173-Diethylamino-N,N-DimethylpropionamideYield 86%

Procedure

In accordance with this example, anhydrous diethylamine (44 grams) and N,N-dimethylacrylamide (60 grams) were heated at reflux temperature (about 56°-60°C.) for 48 hours. After this period of time, the reaction mixture was subjected to distillation to separate unreacted amine and amide followed by recovery of product in 86 percent yield at 70°C. and 2 mm. mercury pressure. The liquid product (purity = about 95 percent is designated herein as Amine Catalyst V, and has the formula, (C2H5)2N-CH2CH2C(O)N(CH3)2. The structure of this novel product was confirmed by infrared functional analysis and purity by gas-liquid chromatographic analysis.

Workup

  1. temperatureat reflux temperature (about 56°-60°C.) for 48 hours
  2. waitAfter this period of time
  3. distillationthe reaction mixture was subjected to distillation
  4. customto separate unreacted amine and amide
  5. customfollowed by recovery of product in 86 percent yield at 70°C.

Sources & evidence

ORD record
ord-b430784cb92d4d9f8d4cdb1a3c5acdce
Source dataset
uspto-grants-1976_05
Patent number
US03954749

Reaction notes

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