Ammonia → N-(3-(Dimethylamino)propyl)methacrylamide

HRID 1732234Notes

Reaction equation

HRID 1732234 reaction equation
[CH3:1][CH:2]([CH2:6]OC)[C:3]([NH2:5])=[O:4].[CH3:9][N:10]([CH3:15])[CH2:11][CH2:12][CH2:13]N.N.[OH-].[Na+]>>[CH3:9][N:10]([CH3:15])[CH2:11][CH2:12][CH2:13][NH:5][C:3](=[O:4])[C:2]([CH3:6])=[CH2:1]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 14798Sodium HydroxideHCID 15535737HCID 15535737, compound

Product 1

HCID 78882N-(3-(Dimethylamino)propyl)methacrylamide

Procedure

117.2 g (1.0 mole) of 2-methyl-3-methoxypropionamide are heated with 107.3 g (1.05 mole) of 3-dimethylaminopropylamine for 20 hours in a temperature range of 145°-175° C. until the evolution of ammonia is complete. The mixture is allowed to cool, 1.5 g of sodium hydroxide is added and the mixture is heated in a high vacuum at 90° to 110° C. The methanol is split off within about 30 minutes, vigorous foaming occurring. The temperature is increased and 122 g (0.72 mole=72% of the theoretical yield) of colorless oil having a Bp0.1 of 106°-110° C. are distilled off.

Workup

  1. temperatureto cool
  2. temperaturethe mixture is heated in a high vacuum at 90° to 110° C
  3. customThe methanol is split off within about 30 minutes
  4. temperatureThe temperature is increased
  5. custom122 g (0.72 mole=72% of the theoretical yield) of colorless oil
  6. customa Bp0.1 of 106°-110° C.
  7. distillationare distilled off

Sources & evidence

ORD record
ord-e5780df588614239b9d8ad4bcaf1cdbd
Source dataset
uspto-grants-1980_12
Patent number
US04237067

Reaction notes

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