Diethylamine → 3-Diethylamino-N,N-Dimethylpropionamide

HRID 596936Notes

Reaction equation

HRID 596936 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]>[Hg]>[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

4

Reactant 2

HCID 8021DiethylamineHCID 17587N,N-Dimethylacrylamide

Product 1

HCID 214492173-Diethylamino-N,N-Dimethylpropionamide

Reagents, catalysts & solvents 1

HCID 23931MercuryCatalyst

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 per cent yield at 70° C. and 2 mm. mercury pressure. The liquid product (purity = about 95 per cent) is designated herein as Amine Catalyst V, and has the formula, (C2H5)2N-CH2CH2C(0)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. customyield at 70° C.

Sources & evidence

ORD record
ord-d8b7d076674b44099a8c548a9386928b
Source dataset
uspto-grants-1977_03
Patent number
US04012445

Reaction notes

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