Stearic Acid → Stearamidopropyl Dimethylamine

HRID 457466Notes

Reaction equation

HRID 457466 reaction equation
[C:1]([OH:20])(=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].[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25][NH2:26]>>[C:1]([NH:26][CH2:25][CH2:24][CH2:23][N:22]([CH3:27])[CH3:21])(=[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

3

Reactant 2

HCID 5281Stearic AcidHCID 7993N,N-Dimethyl-1,3-propanediamine2×

Product 1

HCID 62109Stearamidopropyl Dimethylamine

Conditions

Temperature
180 °C

Procedure

(a-2) was synthesized by a dehydration amidation reaction between stearic acid and N,N-dimethyl-1,3-propanediamine. Specifically, 161 g of N,N-dimethyl-1,3-propanediamine and 373.3 g of the fatty acid were placed in a four-neck flask equipped with a stirrer, a temperature gage and a dehydrating pipe and the mixture was raised to 180° C. The mixture was stirred under heating at this temperature for about 5 hours while distilling generated water. Then, the reaction mixture was cooled to 120° C. and unreacted amine was distilled under reduced pressure to obtain the target N-stearoylaminopropyl-N,N-dimethylamine (a-2).

Workup

  1. customequipped with a stirrer
  2. temperatureunder heating at this temperature for about 5 hours
  3. distillationwhile distilling
  4. temperatureThen, the reaction mixture was cooled to 120° C.
  5. distillationunreacted amine was distilled under reduced pressure

Sources & evidence

ORD record
ord-f9732395f84944939969731142614b8c
Source dataset
uspto-grants-2007_03
Patent number
US07189687B2

Reaction notes

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