Stearic Acid → Stearamidopropyl Dimethylamine

HRID 1835064Notes

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].[BH4-].[Na+]>>[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

Reactant 3

HCID 5281Stearic Acid2×

HCID 7993N,N-Dimethyl-1,3-propanediamine2×

HCID 4311764Sodium borohydride

Product 1

HCID 62109Stearamidopropyl Dimethylamine

Conditions

Temperature: 180 °C

Procedure

(a-5) was synthesized by a dehydrating esterification reaction between stearic acid 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 120 g of N,N-dimethyl-1,3-propanediamine, 284 of stearic acid and 0.12 g of sodium borohydride and the mixture was raised to 180° C. The mixture was heated under stirring at this temperature for about 5 hours while distilling generated water and a part of N,N-dimethyl-1,3-propanediamine to be distilled together with water. The reaction mixture was then cooled to 120° C. and unreacted amine was distilled under reduced pressure (10 torr) to obtain 368 g of the target N-stearoylaminopropyl-N,N-dimethylamine (a-5).

Workup

customSpecifically, a four-neck flask equipped with a stirrer
temperatureThe mixture was heated
distillationwhile distilling
distillationa part of N,N-dimethyl-1,3-propanediamine to be distilled together with water
temperatureThe reaction mixture was then cooled to 120° C.
distillationunreacted amine was distilled under reduced pressure (10 torr)

Sources & evidence

ORD record: ord-108a49581d83463cac47b9048c7f5c5b
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06770617B2

Reaction notes

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