Diethylamine → N,N-Diethyl-2-methylprop-2-en-1-amine

HRID 1455477Notes

Reaction equation

HRID 1455477 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].Cl[CH2:7][C:8]([CH3:10])=[CH2:9].[OH-].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([N:3]([CH2:4][CH3:5])[CH2:7][C:8]([CH3:10])=[CH2:9])[CH3:2]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 112413-Chloro-2-methyl-1-propeneHCID 14798Sodium Hydroxide

Product 1

HCID 13112059N,N-Diethyl-2-methylprop-2-en-1-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

54.86 g (0.75 mol) of diethylamine and 45.28 g (0.50 mol) of 1-chloro-2-methyl-2-propene were dissolved in chloroform (100.14 g), 20.0 g of sodium hydroxide was added, and the system was allowed to react for 15 hours at 70° C. Upon completion of the reaction, the chloroform solution was washed with a sodium carbonate aqueous solution to remove the unreacted diethylamine, diethylamine hydrochloride, and sodium hydroxide, which yielded a chloroform solution of N,N-diethyl-2-methyl-2-propene-1-amine. 150 g of a 4 N hydrochloric acid aqueous solution was added to the chloroform solution, the N,N-diethyl-2-methyl-2-propene-1-amine was converted into a hydrochloride and extracted from the aqueous phase, and the water was removed by freeze drying, which yielded 60.57 g (0.37 mol; 74% yield) of 2-propene-1-aminium, N,N-diethyl-2-methyl, hydrochloride in the form of a white powder. The structure of the 2-propene-1-aminium, N,N-diethyl-2-methyl, hydrochloride thus obtained was confirmed by 1H-NMR (400 MHz)

Workup

  1. customto react for 15 hours at 70° C
  2. customUpon completion of the reaction
  3. washthe chloroform solution was washed with a sodium carbonate aqueous solution
  4. customto remove the unreacted diethylamine, diethylamine hydrochloride, and sodium hydroxide, which

Sources & evidence

ORD record
ord-f946f3fe92fb4790bc37ca256f5bbf1e
Source dataset
uspto-grants-2009_01
Patent number
US07482417B2

Reaction notes

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