N,N-Dimethyl-1,3-propanediamine → Stearamidopropyl Dimethylamine

HRID 1835063Notes

Reaction equation

HRID 1835063 reaction equation
[C:1]([O:20]C)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:22][N:23]([CH3:28])[CH2:24][CH2:25][CH2:26][NH2:27]>CO>[C:1]([NH:27][CH2:26][CH2:25][CH2:24][N:23]([CH3:28])[CH3:22])(=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamine2×HCID 8201Methyl Stearate2×

Product 1

HCID 62109Stearamidopropyl Dimethylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
180 °C

Procedure

(a-2) was synthesized by a de-methanol amidation reaction between methyl stearate and N,N-dimethyl-1,3-propanediamine. Specifically, a four-neck flask equipped with a stirrer, a temperature gage and a dewatering pipe was charged with 161 g of N,N-dimethyl-1,3-propanediamine and 448 g of methyl stearate and the mixture was raised to 180° C. The mixture was heated under stirring at this temperature for about 5 hours while distilling generated methanol. The reaction mixture was cooled to 120° C. and unreacted amine was distilled under reduced pressure to obtain 545 g of the target N-stearoylaminopropyl-N,N-dimethylamine (a-2).

Workup

  1. customSpecifically, a four-neck flask equipped with a stirrer
  2. temperatureThe mixture was heated
  3. distillationwhile distilling
  4. temperatureThe reaction mixture was cooled to 120° C.
  5. distillationunreacted amine was distilled under reduced pressure

Sources & evidence

ORD record
ord-ecad2f2ea9164193b7549cae5b6d5202
Source dataset
uspto-grants-2004_08
Patent number
US06770617B2

Reaction notes

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