Ethyl cyanoacetate → 2-cyano-N-[3-(dimethylamino)propyl]acetamide

HRID 1067870Notes

Reaction equation

HRID 1067870 reaction equation
[C:1]([CH2:3][C:4]([O:6]CC)=O)#[N:2].[CH3:9][N:10]([CH3:15])[CH2:11][CH2:12][CH2:13][NH2:14]>C1(C)C=CC=CC=1>[C:1]([CH2:3][C:4]([NH:14][CH2:13][CH2:12][CH2:11][N:10]([CH3:15])[CH3:9])=[O:6])#[N:2]

Participants

4

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 7993N,N-Dimethyl-1,3-propanediamine

Product 1

HCID 50583022-cyano-N-[3-(dimethylamino)propyl]acetamideYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl cyanoacetate (51.106 g, 0.4518 mole) was added to 3-(dimethylamino) propylamine (46.162 g, 0.4518 mole) in a 250 ml round bottom flask equipped with a magnetic stir bar. After stirring for approximately 0.5 hr, 50 ml of toluene was added. The clear orange liquid was stirred at room temperature for approximately 15 hours, after which the ethanol and toluene were removed via vacuum distillation. 2-Cyano-N-[3-(dimethylamino)propyl]acetamide was obtained in 96% yield.

Workup

  1. customequipped with a magnetic stir bar
  2. stirringThe clear orange liquid was stirred at room temperature for approximately 15 hours
  3. customafter which the ethanol and toluene were removed via vacuum distillation

Sources & evidence

ORD record
ord-433b1c351aab4497821ec99175586d5b
Source dataset
uspto-grants-2001_06
Patent number
US06248801B1

Reaction notes

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