Dimethylamine → 2-(N,N-dimethylamino)ethyl 3-(N',N'-dimethylamino)propionate

HRID 596462

Reaction equation

HRID 596462 reaction equation
[CH3:1][NH:2][CH3:3].[C:4]([O:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])(=[O:7])[CH:5]=[CH2:6]>>[CH3:1][N:2]([CH2:6][CH2:5][C:4]([O:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])=[O:7])[CH3:3]

Participants

3

Reactant 2

HCID 674Dimethylamine2×HCID 171112-(Dimethylamino)ethyl acrylate

Product 1

HCID 214492152-(N,N-dimethylamino)ethyl 3-(N',N'-dimethylamino)propionate

Procedure

Anhydrous dimethylamine (19.8 grams) was added dropwise to 2-(N,N-dimethylamino)ethyl acrylate (31.5 grams) in a magnetically-stirred, ice-cooled reaction vessel at such a rate that the temperature did not exceed 40° C. The addition of dimethylamine was complete in about 10 minutes. After allowing the reaction mixture to stir overnight at room temperature, it was subjected to reduced pressure (about 20 mm. Hg) to remove unreacted dimethylamine. Gas-liquid chromatographic analysis indicated that the residue product was 96.5 percent pure. The structure of the product, ##STR20## was verified spectroscopically (nuclear magnetic resonance and infrared) and by elemental analysis. Anal. Calc'd. for C9H20N2O2 : C, 57.4; H, 10.6; N, 14.9. Found: C, 57.3; H, 10.5; N, 14.8. This product is designated herein as Amine Catalyst X.

Workup

  1. temperaturecooled
  2. customreaction vessel at such a rate that the temperature
  3. customdid not exceed 40° C
  4. customto remove unreacted dimethylamine

Sources & evidence

ORD record
ord-86dd4bb4acca44f1ba1041d71f9bacc6
Source dataset
uspto-grants-1977_03
Patent number
US04011223

Linked notes

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